TW200914579A - Aromatic amine derivative and organic electroluminescent element using the same - Google Patents

Abstract

The present invention provides an aromatic amine derivative with a specific structure, the aromatic amine derivative having loop structures at two sides of the central double bond; and provides an organic electroluminescent element, the organic electroluminescent element clamping one or more organic thin film layers that contains at least one luminous layer between a cathode and an anode, and at least one of the organic thin film layer containing the foregoing aromatic amine derivative; and provides an organic electroluminescent element and the organic electroluminescent element for manufacturing the same and a solution containing an organic electroluminescent material. The solution containing the organic electroluminescent material includes the foregoing aromatic amine derivative and the solvent as the organic electroluminescent material. The organic electroluminescent element has longer a service life, higher luminous efficiency, and can emit blue light with higher color purity.

Description

200914579 IX. Description of the Invention: [Technical Field] The present invention relates to an aromatic face I, - ^, and an organic electroluminescent device using the same, especially for a longer life and higher luminous efficiency An organic electroluminescent device which is high, emits blue light of high purity, and an aromatic amine derivative used for the production thereof. [Prior Art] The industry believes that organic electroluminescent (EL) devices using organic materials have promising materials for solid-state light-emitting large-area full-color display devices. . The fox element includes an illuminating layer and a counter electrode that holds the layer. In the case of light emission, if an electric field is applied between the electrodes, electrons are implanted from the cathode side, and the holes are implanted from the anode side. Further, there is a phenomenon in which the electron is recombined with the hole in the light-emitting layer, and 瀣 μ is generated, and the excited state is restored. When the excited state is restored to the base, the energy is released in the form of light. The conventional organic EL element has a lower driving voltage than the inorganic light-emitting diode and has a lower luminance or luminous efficiency. χ, the characteristic deterioration is also obvious, but it has not been practically applied. Although the organic £1 component has been gradually improved recently, it still requires higher luminous efficiency and longer life. For example, there is no single use of a single bismuth compound as an organic luminescent material. However, in the technique, for example, in the case where the current density is (6), only a luminance of 1,650 cd/m2 is obtained, and an extremely low value of i cd/A is not practical. Further, a technique of using a single-double compound as an organic light-emitting material has been disclosed (Patent Document 2). However, in the _ 132042.doc 200914579, the efficiency is a low value of about 1 to 3 cd/A, and it is necessary to carry out an improvement for practical use. On the other hand, an organic EL device having a long life of using a styrene-based compound or the like is used as an organic light-emitting material (Patent Document 3). However, the life of the component is insufficient and further improvement is required. Further, a technique of using a mono- or di-quinone compound and a di-bromo compound as an organic light-emitting medium layer has been disclosed (Patent Document 4). However, in these techniques, the common roll structure of the styrene compound causes a long wavelength of the luminescence spectrum to deteriorate the color purity. Further, Patent Document 5 discloses a blue light-emitting element using an asymmetric styrene compound. However, although this element has excellent luminous efficiency, its life is not sufficient and further improvement is required. Patent Document 1: Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. 8-126 No. Patent Document No. 3: International Publication No. WO 94/006 No. 157 Patent Document 4 1 _ 2 g 4 〇 5 〇 公报 专利 专利 : : : : : : : : : : 【 【 【 【 【 【 【 【 【 【 【 【 【 【 【 【 【 【 【 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本An organic EL device having a long lifetime, high luminous efficiency, and capable of emitting blue light having a high color purity, an aromatic amine derivative for producing the same, and a solution containing an organic EL material. Technical Solution for Solving the Problem 132042.doc 200914579 The present inventors have developed an organic EL element having a top material and using the same, and reversing the enthalpy, and the aromatic amine derivative has been studied for a long time. The above-mentioned target aromatic amine can be obtained by a specific berry derivative represented by the following general formula (1). Upon completion of the knowledge, the present invention provides the following organisms. Aromatic amine derivative expressed by flying u) [Chemical 1]

[wherein, R 丨 R R 2 independently represent a hydrogen atom having a carbon number of 1 to 5 Å, which is produced by the aryl group which is deuterated or unsubstituted. 2. The carbon number of the substituted carbon is 5~50 R~R, respectively, which represents the substituted or unsubstituted alkyl group, and the number of carbon atoms substituted or unsubstituted. The name of 5 to 5 Å | substituted or unsubstituted heterocyclic group having a carbon number of 5 to 50. The earth or the obtained Ar2 each independently represents a substituted or unstretched aryl group, a substituted or unsubstituted number of 5 to 50 groups, or a group represented by the above formula (4). a 5- to 5-fold heterovalent heterocyclic ring {in the formula (A), the Αγ3 and the Ar4 fraction of 5 to 50 are unsubstituted or unsubstituted carbon or the substituted or unsubstituted carbon number is 5~ 5〇132042.doc 200914579 2 is a heterocyclic group, and R7 represents a substituted or unsubstituted carbon group of a 5-alkyl group, -〇_, _S-, -S02-, _SiR8R9-, -NR 0-(R8, R9 and R10 each independently represent a substituted or unsubstituted alkyl group having a carbon number of 5 Å or a substituted or unsubstituted aryl group having a carbon number of 5 to 5 Å)} a and b is independently an integer of 1 to 3. When a is 2 or more, a plurality of Ar 1 may be different. When b is 2 or more, a plurality of Ar2's may be the same or different. R and R, R1 and Ar1, R2 and Ar2, R3 and R4, R^R6, Ar> R5 and 7 or R0, Ar2 and R3 and/or R4 may be bonded to each other to form a single body, thereby forming a saturated or not Saturated ring. 2, wherein, when R3 to r6 are unsubstituted phenyl groups, there is no Ar 丨 and the same is not, and the substituted 1, 4 phenyl or fluorene, 4 - stilbene group]. Moreover, the present invention provides an organic EL device comprising a layer of an organic thin film comprising at least one layer or a plurality of layers of a light-emitting layer, and at least a layer of the organic film layer containing the aromatic amine derivative. Further, the present invention provides a solution containing an organic EL material containing the above aromatic amine derivative and a solvent as an organic EL material. EFFECTS OF THE INVENTION The sedative element of the aromatic amine derivative of the invention can be used in a practical manner to obtain sufficient illuminance and luminescence, and it is not easily deteriorated for a long time, and has a long life. [Embodiment] The aromatic amine derivative of the present invention is a compound represented by the following formula (1): 132042.doc 200914579. [Chemical 2] N~(-Ar1)

(A)

In the general formula (I), R丨~R2 are independently represented by the >& oxime atom, substituted or unsubstituted alkyl group having a carbon number of 1 to 50, or ^^ 3 6 fly test, left replacement Or an unsubstituted aryl group having a carbon number of 5 to 5 Å, and r3 to R6 each independently represent an unsubstituted or unsubstituted fluorene group, and the substituted or unsubstituted carbon number is 5~ The 5-aryl group or the substituted or unsubstituted heterocyclic group having a carbon number of 5 to 5 Å.

The carbon number of the ring of R6 is a group of (10), preferably an alkyl group having a carbon number of (9), more preferably an alkyl group having a carbon number of (7), and examples thereof include a methyl group and an ethyl group. Propyl, isopropyl, butyl, t-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, octadecyl, 2-phenylisopropyl, trichloromethyl, di Fluoromethyl, benzyl, α-phenoxybenzyl, α,α-dimethylbenzyl, α,α-methylphenylbenzyl, α,α-bis(trifluoromethyl)benzyl, Triphenylmethyl, OC-benzyloxybenzyl, and the like. The aryl group having 5 to 50 carbon atoms (preferably, a carbon number of 5 to 20) of R1 to R6 may, for example, be a phenyl group, a 2-f-phenyl group or a 3-methylphenyl group. , 4-methylphenyl, 4-ethylphenyl, biphenyl, 4-f-biphenyl, 4-ethylbiphenyl, 4-cyclohexylbiphenyl, triphenyl, 3,5 _Dichlorophenyl, naphthyl '5-methylnaphthyl, 1-naphthyl, 2-naphthyl, anthracenyl, fluorenyl, fluorenyl, 132042.doc 200914579 chopsticks (chrysenyl), phenanthryl, 9 — τ 苐 苐-1-yl, 9,9-dimethyl-2-yl, 9,9-dimethyl 葙Α Λ 丫 丫 3- 3- base, 9,9 dimethyl _4· Base. Examples of the heterocyclic group having a carbon number of 5 to 5 Å (preferably a heterocyclic group having 5 to 2 carbon atoms) of R3 to R6 include, for example, hydrazine and σm. Sitting, Π ratio; U, 〇 喃, thiophene, benzothiophene, 吟 _ porphyrin, porphyrin, carboazole, pyridine, quinoline, isoquinoline, benzoquinone, ... Residues such as imidazolium and piperidine. In the general formula (1), R1 and R2 may be inclined to ± with respect to the center -c = c-, and are located at the cis or trans position. In the formula (I), Af and Ar4 are each independently a substituted or unsubstituted aryl group having a carbon number of 5 to 5 Å, a substituted or unsubstituted carbon group having a carbon number of (4), Or the group represented by the above formula (A). Examples of the exoaryl group and the heterocyclic group of Afl to V include an example in which the aryl group or the heterocyclic group described in the above R1 to R6 is divalent. Further, when ArW is an aryl group, a condensed ring is preferred. When ruthenium is phenyl, 'Ar2 is preferably a condensed ring, preferably a naphthyl group, a benzyl group, a 9,9 dimethyl fluorene+ group, a 9,9-dimethyl 2nd yl group, and a 9 9 group. Dimethyl-3-yl, 9 9-dimethyl-4-yl. In the general formula (A), Ar and Ar each independently represent a substituted or unsubstituted aryl group having a carbon number of 5 to 5 Å or a substituted or unsubstituted carbon number of 5 to 50. a cyclic group, R7 represents a substituted or unsubstituted alkylene group having a carbon number of 1 to 50, -Ο-, -s_, _s〇2_, _SiR8R9, _nr1〇_ (r8, R9 and R1G independently represent substituted Or the unsubstituted carbon number is 丨~ young alkyl group, or substituted or unsubstituted aryl group having a carbon number of 5 to 5 )), as an example of 132042.doc -11 - 200914579 each base, In the same general formula (1) as the above-mentioned groups of 1-6, Ar丨 and Ar2 are preferably each independently the same as the group of the formula (4), and are represented by the formula (4). Wherein, m is a substituted or unsubstituted surface of 5 to 5 Å, or a substituted or unsubstituted carbon number of 5 to 50 2 valent heterocyclic groups, preferably Ar1 It is different from Ar2. In the formula (1), 4 b is independently an integer of 3 . When the above is above, the ^ can be the same or different. When _ is above, a plurality of Ws may be the same or different. Further, R1 and R2, R1 and Ari, r2盥2 3 K, Ar, R and R4 ' R5 and R6, Ar1 and R and/or R6, Ar2 and R3; 5 / + D 4_p, , ^ may be different Bonded and joined to each other to form a saturated or unsaturated ring. Examples of the formation of the coating of R1 and R2 include a cyclopentene and a cyclohexa. As R1 and Ar2, R2 disc Ar2 knot # f丄 — /, key, ,,. Examples of the ring formed are: imprinted, dihydronaphthalene, naphthalene, and the like.

Examples of the ring formed by bonding R3 and R4, and R5 and R6M^ may, for example, be carbazole. Examples of the ring formed by bonding Ar1 to R5 and/or R6 2 t and Ar to R and/or R4 include, for example, carbenazole. Wherein, in the formula (I), R3 to the support K are both unsubstituted phenyl groups and when a = b = 1, the "m" is an unsubstituted M_phenylene group or m. ', 132042.doc 12 200914579 The aromatic (tetra) organism of the present invention preferably has a structure satisfying the following contents in the above formula (1). [wherein R R , Ar and Ar 2 are each independently the same as described above. (In the formula (A), W and Ar4 are each independently the same as above, and R7 represents, each, -so...iRV...Nr10_ (r8, 尺9, and Ri〇 are each independently substituted or unsubstituted carbon number is 1~ 5's base' or substituted or unsubstituted aryl group having a carbon number of 5 to 5 ))) a and b are each independently an integer of 丨. R1 and R2 may be bonded to each other to form a ring. Wherein, there is no case where an aromatic ring is formed. Among them, none of Ar1 and Ar2 are substituted or unsubstituted, phenyl, M-thylene, 2,6-naphthyl, 9,1 〇 The situation of 蒽基. Further, the aromatic amine derivative of the present invention preferably has a structure which satisfies the following contents in the above formula U). [wherein, R1 to R6 are each independently the same as described above. /r1 is a group represented by the above formula (A). In the formula (8), A〆, a〆 and R are each independently the same as described above. }.

Ar is independently a substituted or unsubstituted aryl group having 5 to 5 carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 5 carbon atoms. a is an integer of 1 to 3, preferably 1. b is an integer of 2 to 3. R and R may be bonded to each other to form a ring. Among them, the case of forming an aromatic ring is excluded. Further, the aromatic amine derivative of the present invention preferably has the structure represented by the following formula (11) to (XVIII). 132042.doc -13- 200914579 General formula (π) [Chemical 3]

[In the formula, 1111 to 1112 are independently the same as 111 to 112, respectively. R13 to R16 are independently the same as R3 to r6.

Ar and Ar· each independently represent a substituted or unsubstituted condensed ring group having a carbon number of 10 to 50. Preferred is a substituted or unsubstituted condensed cyclic group having 10 to 20 carbon atoms, more preferably a substituted or unsubstituted condensed cyclic group having 10 to 14 carbon atoms. Among them, there is no case where Arn and Afl2 are the same.

Rn and R12 may be bonded to each other to form a ring. Among them, there is no formation of an aromatic ring. ] ^ As a condensed cyclic group represented by Ar" and Ar12, there are two substituted substituted Caiji, 2,6_caiji, 2,7_caiji, 2,5-caiji, =naphthyl , 9,1〇_蒽基,丨,4·Onion base, 2,6_蒽 base, 6,12- disease base,, phenanthryl, 1..., Youji training base, 7,12_Benzene: 7, (4) Benzyl, benzophenanyl, preferably 丨, 4 naphthyl, ^ tomb base, 2,7-naphthyl, w onion, 6, called base, 16 = base, & 7,12_Benzene onion ", 1 combined with benzene, 2,7-linked benzene. ^ soil, 1,4- general formula (III) [Chemical 4] 132042.doc 200914579 β» CKI) J [wherein, R11 〜1〇 ( > separate j B and A ring and B ring respectively or not The substituted carbon has a condensed cyclic group of a substituted naphthalene residue having a skeleton of a naphthalene residue. It is preferred to have a 1,4 ring group, and the substituted or unsubstituted carbon number of the oxime is ig~2g. The condensed carbon number of the carbon number of the naphthalene residue has a substituted or unreacted condensed ring group of 10 to " Β B f independently represents a hydrogen atom and an alkane having a carbon number of 1 to 4. Base, carbon number '\6% alkyl group, carbon number 6 to 16 aryl group. Among them, Βι and Β6, Β2 and B3 'B, B4, B4 and B5, B7 and B12, Μ and Β9, β> 11, β10 and Β 1 1 - έ θ ι, ί , ' can be linked to each other to form an unsaturated ring, the unsaturated %: the knife independently has a hydrogen atom, an alkyl group having a carbon number of 1 to 4, and the carbon number is 5 to 6% of an alkyl group and an aryl group having a carbon number of 6 to 16. Among them, the indole ring and the anthracene ring are the same. R" and can be mutually joined to form a ring. The towel does not form an aromatic ring.] 11

As a ring A formed by mutually connecting β1 and Β6, B2 and Β3, B3 and Β4, B4 and B5, and B7 and Β12, B8 and Β9, B9 and Β10, B10 and B11 are mutually connected to each other. Examples of the B ring formed by joining may be selected from the examples of Ar and Ar12 described above. Examples of B) to B12 and the alkyl group and the aryl group which may be formed by the unsaturated ring which can be formed include an example of a suitable carbon number in the group of rLr6, which is exemplified by Examples 132042.doc -15-200914579. Or a cyclohexyl group, etc. (IV) [Chemical 5] As an example of a cycloalkyl group, a cyclopropyl cyclopentyl group is mentioned.

R: 1 to R16 are each independently the same as described above. c:c & independently represents a hydrogen atom, an alkyl group having a carbon number of μ, a nucleus of a broad 6 aryl group, an aryl group having a carbon number of 6 to 16, c, c, C4, c, c5, c7-c. iS L and C can be interconnected to form and ". Further, the unsaturated ring may independently have a chlorine atom, a carbon number: (four), a carbon number of 5 to 6, and a carbon number of 妒 and R12 may be bonded to each other to form a ring. Shape 2: Base. shape. ] * There is no formation of an aromatic ring as an example of the condensation of C1 and C6, C2 and C3, c, c4, and the formation of the A ring, and the group is connected to the whistle base, and c7 and c12. : A material of the B ring formed by the groups being connected to each other, and an example of Ar12. Examples of Cl to c12 and the above-mentioned unsaturated ring I can form a ring, a cyclodyl group and an aryl group can be exemplified by the same formula as β1 to decane. The base phase listed in the hall (V) 132042.doc 16- 200914579 [Chem. 6]

Π16 is independently the same as above. The A ring and the B ring public μ i independently represent the substituted or unsubstituted carbon number of 1 0 ~ 50. Preferably, the substituted or unsubstituted condensed ring having a carbon number of 10 to 20 is more preferably a substituted or unsubstituted condensed ring group having a carbon number of 10 to 14. D1 to D14 are independent of each other _ independent table is not a hydrogen atom, an alkyl group having a carbon number of 1 to 4, a carbon number of 560%, an aryl group having a carbon number of 6 to 16, DkD6, D2盥D3 & ❹W and ^, ^^ with ^ (four) knot formation is not Γ: it:. Further, the unsaturated ring may independently have a chlorine atom, a cycloalkyl group having a carbon number of η Ί, a number of 5 to 6, and an aryl group having a carbon number of 6 to 16.

K.J R and R may be linked to each other to form a ring. Among them, no aromatic shape is formed. ] '月连:: is a combination of D1 and D6, D2 and D3, D3 and D4, D4 and D5: the formation of the knot, the formation of the B ring formed by the combination of ~ and D: The above CM is connected as an example of D丨~D" and such an example of a non-saturated ring group, a cycloalkyl group, and an aryl group. For example, the same as β1 to Β can be cited. The base phase of the π force method (VI) 132042.doc 17· 200914579 [Chem. 7]

RU to Rl6 are independently the same as described above. The A ring and the B ring respectively represent a substituted or unsubstituted condensed ring of 10 to 50, and the substituted C ring is preferably a substituted or unsubstituted carbon number of 10 to 20. The substituted or unsubstituted condensed ring group having a carbon number of 1 〇 to 14 is used. The scorpion scorpion does not independently represent a hydrogen atom, an alkyl group having a carbon number of 1 to 4, a cycloalkyl group having a carbon number of 5 6 , an aryl group having a carbon number of 6 to 16, Ε1 and Ε6, Ε3 and Ε4, Ε and Ε, Ε7 and Ε" can be interconnected to form an unsaturated ring. Further, the % unsaturation may independently have a hydrogen atom, an alkyl group having a carbon number of 丨4, a cycloalkyl group having a carbon number of 5 to 6, and an aryl group having a carbon number of 6 to 16. u R and R may be joined to each other to form a ring. Among them, there is no formation of an aromatic ring. An a ring formed by interconnecting E and Ε, E and E4, and a B ring formed by connecting 〇 and Ε11, E7 and E14 to each other, may be selected from Examples of the above Ar11 and Ar12. Examples of the alkyl group, the cycloalkyl group and the aryl group which are contained in E to E14 and the unsaturated ring which can be formed are the same as those exemplified for B1 to B12. General formula (VII) 132042.doc 18- 200914579 [Chemical 8]

R is independently the same as above. The A% and the 3 rings independently indicate that the number of annihilation numbers that have been substituted or not reduced by 1 〇 to 50 is the clothing base. Preferably, the substituted or unsubstituted carbon number 1 10~20 condensation is earned| ^ 丨~< the recovery number is, soil, and more preferably the substituted or unsubstituted carbon number 10~14 condensation Ring base. The number F is independently represented by a hydrogen atom, the carbon number is 5-base, and the carbon number is aryl, ~, ~

And F 4 and F5, F8 and AW and F13, F" disk F?T are connected to form a ring and the ring... The unsaturated ring can be independently: with an atom, a slave with a W alkyl group, the carbon number is 5 to 6 cycloalkyl, 6:? aryl. RU and Rl2 may be linked to each other to form a ring. Among them, there is no case of forming an aromatic ring. ] Battle As F1 and ^^^^^~ A ring formed by any group, and #和^, 4〇 and 41,?丨 2 and? 13. An example of the B ring formed by connecting any one of the groups to each other may be selected from the above Ar12. Examples of the alkyl group, the cycloalkyl group, and the aryl group which are contained in the unsaturated ring which can be formed by F1 to F", and the like are the same as the examples of the beautiful phase 132042.doc -19-200914579 listed in b1 to bU. . General formula (VIII) [Chemical 9]

Rl: ~R16 are independently the same as described above. A soil and B ring are respectively unsubstituted or unsubstituted condensed ring groups having a carbon number of 10 to 50. 1Λ , a preferred fluorene-substituted or unsubstituted condensed ring group having a carbon number of 10 to 20, 々 1 , , _ 疋 is a substituted or unsubstituted condensed ring group having a carbon number of 10 to 14. η G1 to G14 are each independently represented by 5 ^ "wind atom, an alkyl group having a carbon number of 1 to 4, a carbon number of 5 to 6, a aryl group, a skirt 8 being an aryl group of 6 to 16, G1 and G6. , G3 disk G4, G8 and G, Gl. With Gu ”

L ^ . 3- . /, G, G, and G7 may be bonded to each other to form an unsaturated %. Moreover, the non-j Ρ A clothing can have a hydrogen atom, a carbon number of 1 to 4, and a carbon number of 5 to 6 independently.

Rn^R12-r ^ , an alkyl group and an aryl group having a slave number of 6 to 16. κ兴R can be connected to each other. ] ready-to-wear. Among them, there is no formation of an aromatic ring as Gl and G6, G3 and G4, g8 9 ^ Αί, n „10 , and any group of G is connected to each other to form A%'m, gu, g, g13, g14 ^ ^ r, 〇 〇 — - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - The same example of the alkane I32042.doc -20- 200914579 base, ring-density group and aryl group possessed by the ring. The base phase of the formula (IX) enumerated with β1~β, 2 [Chemical 10]

R"~R16 are independently the same as above. The anthracene ring and the anthracene ring respectively represent a condensation of 10 to 50, and the carbon number of the hi-substitution is dΜ. Preferably, the condensed cyclic group is substituted or not 10 to 20, and more preferably a hydrazine substituted or a condensed cyclic group of 10 to 14 is not taken. The inverse of Η1 to Η16 independently represents chlorine. s ', sub, and an anion number of 1 to 4, a cycloalkyl group having a carbon number of 5 to 6, and a carbon number of extinction number #. ^丨^ u The square base, Η, Η8, Η, Η5, Η and Η, Η2 and Η13,; "14, #'#," .. ν, Η and Η can be interconnected to form an unsaturated. The unsaturated ring has a hydrogen atom, an alkyl group having a carbon number of 1 to 4, a mountain alkyl group having a carbon number of 5 to 6, and an aryl group having a stone inverse of 6 to 16. R and R may be used. They are joined together to form a garment. Among them, there is no case of forming an aromatic ring.] As a ring formed by the connection of Η, Η, Η and Η, W and Hl1, Hl2 and Η" 'Hl4 and Η, An example of a B-ring formed by joining any one of Η and # may be selected from the above-mentioned examples of gossip and gossip. 132042.doc -21 . 200914579 An example of the alkyl group, the alkyl group and the aryl group which may be bonded to the unsaturated ring formed by the two groups, and the like, may be exemplified by the same examples as Βΐ~β12. General formula (X) [化11] (x>, gorge [wherein, R21 to R22 are independently the same as Ri~R2

R 23~1? 26 R26 is independently the same as R3~R6, respectively. R27 means SO- Ο R29 r3. VIII(1) SiR2V9_, -NR3°-(R28, ΓΑ2 independently represents a substituted or unsubstituted carbon group of (4), or a substituted or unsubstituted carbon number of 5 is substituted or unsubstituted And the number of carbon atoms of 1 to 20, or the substituted or unsubstituted carbon number of 5 to 2 〇 is W, or the second is substituted or Not for the 5 to 10 aryl.). _ and substituted or unsubstituted carbon number R21 and R22 can be joined to each other to form a shape. ] /, Medium 'There is no formation of an aromatic ring. The alkyl group and the aryl group of R28 to R3G. The general formula (XI) is the same as r1 to r6. [12] 122042.doc •22· 200914579

R31 to R32 are independently the same as R1 to R2. R33 to R36 are independently the same as r3 to R6. R37 and R38 represent -〇-, _s_, _S〇2_, -SiR131R132_, _nr133

(R, Rl32, and Rl33 each independently represent a substituted or unsubstituted aryl group having a carbon number of 1 to 50 or a substituted or unsubstituted carbon number of 5 to 5 Å. Preferably, it is represented. The substituted or unsubstituted carbon number is an alkyl group of 丨~", or a substituted or unsubstituted aryl group having a carbon number of 5 to 2 Å. More preferably, the carbon is unsubstituted or unsubstituted. The number is an alkyl group, or a substituted or unsubstituted aryl group having a carbon number of 5 to 1 Å.) wherein no r37 and KM are the same. R and R may be bonded to each other to form a ring. Except for the case where an aromatic ring is formed.] As an example of R13 and 132, it is also the same as R1 to R6. Formula (XII) [Chem. 13]

R41 to R42 are independently the same as R1 to R2. R43 to R46 are independently the same as r3 to r6. 132042.doc •23· 200914579 2 47 Tables 〇··, _s_, _s〇2...SiRl4lRl42·, _nr143_(r..., f42 1143 respectively, iL represents the substituted or unsubstituted carbon number (4), or The substituted or unsubstituted aryl group having a carbon number of 5 to 5 Å. It is preferably a substituted or unsubstituted carbon group having a carbon number of U or a substituted or unsubstituted carbon number of 5 More preferably, it is a substituted or t-substituted carbon group having a carbon number of 1 to 1 fluorene or a substituted or unsubstituted aryl group having 5 to 10 carbon atoms. , indicating that the substituted or unsubstituted carbon number is (4). Preferably, it is a (tetra) group of 1 to 2 G, and more preferably a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms. R and R42 may be bonded to each other to form a ring... without forming an aromatic ring. As an example of R141 to R143, it is the same as R1 to R6; as an example of the extension of R, it can be listed as R~R. An example in which the alkyl group becomes a 2-valent group. General formula (XIII) [Chem. 14]

R51 to R52 are independently the same as r1 to r2. R53 to R56 are independently the same as R3 to Μ. 153 15 1

-NR1:>MR R represents 0-, _s_, _s〇2, __151&152 132042.doc -24- 200914579 U 1 5 2 τ>153 v , R is independently represented by substituted or unsubstituted carbon number It is an alkane f of 丨~5〇, or a substituted or unsubstituted aryl group having a carbon number of 5 to 5 Å. Preferably, the substituted or unsubstituted carbon number is an alkyl group of 丨~汕, or a substituted or unsubstituted aryl group having a carbon number of 5 to 20. More preferably, it is a substituted or unsubstituted carbon group having a carbon number of 5 or 10, or a substituted or unsubstituted carbon number of 5 to 10. ). ,work

Ar52 represents a substituted or unsubstituted carbon| is a condensed ring group of ι〇~5〇. It is preferred that the substituted or unsubstituted carbon number is 1 () to fluorene = base, and more preferably the substituted or unsubstituted carbon number is from 1 to 14: Moreover, R52 can be interconnected to form a ring. In the case of the oxime, no aromatic ring is formed. Examples of the aryl group and the aryl group of R to R153 are the same as those of r1 to r6. Examples of the condensed ring group represented by Ar52 are the same as those of Arll and Ap. General formula (XIV) [Chem. 15]

L Formula 1f 'R61 to R62 are independently the same as ri~r2. R63 to R66 are independently the same as R3 to r6.

Ar61 represents a condensed oxime with a carbon number of 1〇~50 substituted by Wah.

base. Preferably, it represents a divalent enthalpy of enthalpy + + L shells < left substituted or unsubstituted 1,4-naphthyl, I32042.doc -25· 200914579 2.6-naphthyl, 2,7-naphthyl, 2,5-naphthyl, naphthyl, 9, ι〇ι, 1,4-mercapto, 2,6-fluorenyl, 6,12-carbyl, 9,l-fluorenyl, j 6 : 2.7 - a radical, a base, 7,12_benzoyl, 7,1〇_, a base, and a [k] fluorenyl group, more preferably a 1,4.naphthyl group, a 2,6-naphthyl group, a 2 7" 9 , 1〇-fluorenyl, 2,6-fluorenyl, 6,12-carbyl, 1,6-youji, 2,7^^ Μ-youji, 7,12-benzofluorenyl, fluorenyl, w, Three 'base, combined with three benzene. , 2,7_

Ar62 is a substituted or unsubstituted phenyl group, and preferably n-R61 and R62 may be bonded to each other to form a ring. Where: base. shape. ] ‘,、, forming a square incense ring, general formula (XV) [Chem. 16]

R71 to R72 are independently the same as ri~r2. W6 is independently the same as R3 to R6. R2 is not 〇, _S·, -S〇2·, -SiR171R172·, _NRm (Rm R172, Rl73 are independent of n - nr -(R ,

The carbon number of the unsubstituted or unsubstituted carbon is idO, and the carbon number of the unsubstituted or unsubstituted is 5 to 5. The aryl group. Preferably, the enamel is replaced by a substituted or unsubstituted aryl group having a carbon number of 1 to 2 Å or a substituted or unsubstituted number of 5 to 2 Å. More preferably, it is an aryl group having a carbon number of 5 to 10 Å which is substituted with or substituted for 1 to 10 or substituted or not substituted by 132042.doc -26·200914579. ).

Ar is a substituted or unsubstituted phenyl group. R71 and R72 can be joined to each other to form a ring. Among them, except. It is preferred that 1,4-benzene is formed into an aromatic ring in the same manner as R1 to R6. Examples of the alkyl group and the aryl group of R171 to R173 Formula (XVI) [Chem. 17]

R81 to R82 are independently the same as R1 to R2. R83 to R86 are independently the same as r3 to r6. = table = substituted or unsubstituted carbon number is i, which is better (better

R 83 is independently a substituted or unsubstituted anthracene of 1 to 2 G, more preferably a substituted or unsubstituted anthracene having an inverse number of 1 to 5, or ...- S-, _s〇2_, _SiRl8lRl82. '-NR183.(r181 λ r182 λ r183 ', /·, an alkyl group having a carbon number of 1 to 5 Å, or a substituted or unsubstituted carbon number of 〜5〇 The aryl group preferably represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 5 to 2 carbon atoms. More preferably, it is represented. A substituted or unsubstituted carbon number y~i〇, an unsubstituted or unsubstituted aryl group having a carbon number of 5 to 1 Å.). Αι·82 represents a substituted or unsubstituted aryl group having a carbon number of 5 to 5 Å, or 132042.doc •27·200914579 A substituted or unsubstituted carbonaceous heterocyclic ring having a carbon number of 5 to 50 base.珏 is an integer of 1 to 3' is preferably 2. b is an integer of 2 to 3. R71 and R72 can be far from each other: gentleman, connected, ,. Form a ring. Among them, no shape forms an aromatic ring. As an example of the R-based base, an example in which the above R1 to R% alkyl group is a divalent group is exemplified. D is an example of the alkyl group and the aryl group of RR, and is the same as r1 to r6, and examples of the aryl group and the heterocyclic group having 1 to 1, wherein the aryl or heterocyclic group described above is changed to 2 An example of a price base. General formula (XVII) [Chem. 18] hx2; ^Sc^LrHr<R:

Cxvn) R

[in the formula,

L R91 to R92 are independently the same as ri to r2. R93 to R96 are independently the same as R3 to R6. R97 represents a substituted or unsubstituted carbon number recognizing an alkylene group having a number of from 1 to 50 (preferably an alkylene group having a number of turns of from 1 to 20, more preferably Β ζ 石山^ 1 good reading The substituted or unsubstituted inverse number is 1 to 5, or _〇_, Λτ 19, and the fly has 'S' ' -S02- . -SiR191R192-, -nr _(Rl91, Rl92, Rl93 respectively The helmet & , the substituted or unsubstituted carbon group, or the substituted or unsubstituted carbon number is 5 to 5. The ~ each independently represents a single bond, a chlorine atom, and a carbon number - 132042.doc • 28- 200914579 The aryl group with a carbon number of /6, Wei is 6~16. Its towel, X] and X and χ, χ3 and χ4, χ5 and Χ6, χ6 and χ7, Χ7 and X8 _. And the above may be linked to each other to form an unsaturated ring. Further, the unsaturated ring may have a single bond, a hydrogen atom, an alkyl group having a carbon number of 4, a ring having a carbon number of 5 to 6, and a carbon number of An aryl group of 6 to 16. The substituted or unsubstituted aryl group having 5 to 5 Å carbon atoms, substituted or unsubstituted, has a divalent heterocyclic group having a carbon number of 5 to 5 (). 3 is an integer of 1 to 3, and preferably ϋ is an integer of Η, Preferred is 1 to 2. R shape and connected to each other to form a ring R can be formed without feeling H of aromatic ring

Ft I

Examples of the stretching base of R97 include an example in which an upper alkyl group is a divalent group. UM: 193 (4) and an example of an aryl group, which is the same as the heart; as an example of the compound: a group of the exfoliation group and the heterobasic group, the aryl group or the heterocyclic group described in the above R1 to R6 can be exemplified. An example of a 2 valence base. General formula (XVIII) [Chem. 19]

[wherein, R101~R102 are independently the same as R1~R2, respectively. R103~R106 are independently the same as R3~R6 respectively. 132042.doc •29· 200914579 R107 and independently unsubstituted or unsubstituted carbon 1~50 The alkyl group (preferably, the number of alkylene groups having a number of 1 to 20, more preferably substituted or unsubstituted carbon atoms having a number of carbon atoms of 1 to 5), or 〇_, , cn —, c:n 191τ^ IQ? -NR193-(r191, r192, r193 are respectively substituted by -, -S〇2-, -SiR191R192_, and the carbon number is 50 alkyl, or An aryl group having a carbon number of 5 to 50 which is substituted or substituted. Wo, and two X11~X18 and X21~X28 respectively think that the single bond, the hydrogen atom 'the alkyl group with a carbon number of 1 to 4, the carbon number of 5 to 6 and the carbon number are 6 ~16 aryl. I, X11 and X12, X12 and χ13^, X13 and X14, χΐ5 and X丨6, χ16 and X17, X17 and X18, X21 disk X22 v22 t , Xing/, x, X22 and X23, X23 and X24, χ25 Any one or more of 盥X26, X26 and X27, 乂27盥28 are bonded to each other to form an unsaturated ring. Further, the unsaturated ring can be a single phase, a hydrogen atom, a carbon number of 1 to 4, a carbon number of s < a cycloalkyl group having a number of 5 to 6; An aryl group having a carbon number of 6 to 16. a is an integer of 1 to 3, a better county], ^ 疋1. b is an integer of 1 to 3, preferably 1 ° ruler 101 and Rl 〇 2 may be mutually connected /%. Among them, there is no case of forming an aromatic ring. As an example of the k and T rolls of R] 07 and R1G8, an example in which the alkyl group described in the above R1 to R6 is a divalent group is exemplified. Examples of the alkyl group and the aryl group of R191 to R193 are the same as those of r1 to r6. Preferably, in the above formula (π) to (χνιπ), r13 to r16, AW, R33 to R36, R43 to r46, and heart ", R73 to R76, R83 to R86, and R93 to r96 K to R are Unsubstituted benzene 132042.doc -30 - 200914579. The substituent which further substitutes each of the groups of the formulae (I) to (XVIII) may, for example, be an alkyl group (preferably, the carbon number is 丨~) More preferably, the carbon 2 is 1 to 20, and particularly preferably the carbon number is 〖~〗 〇, for example, methyl, ethyl, isopropyl, tert-butyl, n-octyl, and Mercapto, n-hexadecyl; ", cycloalkyl (preferably, the carbon number is 3 to 30, t is preferably a carbon number of 3 to 20, particularly preferably a carbon number of 3 to 1 (), For example, a cyclopropyl group, a cyclo n-pentyl group, a cyclohexyl group, etc.), a dilute group (preferably, the carbon number is 2 to 30, more preferably, the carbon number is 2 to 20, and particularly preferably, the carbon number is 2 to 1 (), for example, ethylidene, allyl, 2-butenyl, 3-pentane, ^, ^^, fluorenyl, etc.), alkynyl (preferably carbon 2 " I prefer that the carbon number is 2~2〇, especially the carbon number is the carbon number two or two. a propyl group, a 3-phenyl group, or the like, an aryl group (a preferred anthracene number is 6 to 30, more preferably a carbon number of 6 to 2 Å, particularly preferably 6 to 12, and examples thereof include a phenyl group, P-methylphenyl, cage A =, etc.), amine group (preferably carbon number 〇~3〇^ keyou 1 good 杲妒 helmet better 疋 carbon number is 0~2〇, ϋ w =, for example, an amine group, a methylamino group, a toluene, etc., a di- or di-amino group, a diphenylamino group, a -f-based amino group, etc.), an alkoxy group (a preferred soil one: The number of charcoal is (4), especially the carbon number is Μ人0, f is better, ethoxy, butoxy, 2-ethylhexyloxy, etc. = carbon number is 6~30, better The carbon number is ^ aryloxy (preferably 6 to; 12, for example, phenoxy, 1 茇). The carbon number is aryloxy (preferably, the carbon number is two. The base number, the naphthyloxy group, and the like are preferably a carbon number of, for example, a carbon number, a 132042.doc ratio of a pyridyloxy group, a pyridinium '31-200914579 group, a pyrimidinyl group, and a quinine group. Alkyloxy group, etc., a mercapto group (preferably π 1 to 3 Å, more preferably a carbon number of 2 Å, particularly preferably a carbon number of For example, acetyl group, benzamidine group, formamidine group, tri-anthracene, fluorenyl ethyl ketone group 2. XT: base (preferably, the carbon number is 2 to I, and the latter number is ~ It is preferably a carbon number of 2 to 12, for example, a methyl group, an ethoxy group, or the like, and an aryloxy group (preferably, the carbon number is thiol rebellion = the carbon number is 7). ～20, particularly preferably, the carbon number is Μ, exemplified by a fluorenylcarbonyl group, etc.), a decyloxy group (preferably, the carbon number is 2 to 30, and the carbon number is 2 to 2 Å, particularly preferably The number of obstacles is 2 to 1. For example, it can be listed as a decyloxy group, a benzyloxy group, or the like, and a guanamine group (preferably, the carbon number is 2 3 〇, more preferably, the carbon number is 2, and particularly preferably the carbon number = Ethylamino group, cage field #, for example, cannonamide, etc.), alkoxycarbonylamino group (preferably, the inverse number of vermiculite is 2 to 3 Å, more preferably 2 to 20 carbon atoms, especially Good 曰 2~12, for example, Lexing $ — # 八, 反石反数 is (better carbon number is 7~3 虱 虱 carbonyl amine group is carbon number as pi carbon number is 7, especially A good base (preferably, the carbon number is Μ / = oxoamine, etc.), the amine is indeed a carbon number of 1 to 2 〇, especially good, etc.), an amine sulfhydryl group (better / * A succinyl amine, benzene continuation amine 〇 ~ 20, particularly good carbon is better, the number of 疋 slaves is methylamine sulfonyl, dioxin:: 12, for example, amine sulfonamide, Sulfhydryl (preferably carbon number soil sulfonyl group, phenylamine sulfonyl group, etc.), amine is 1 to 3 〇, 〇 is good, carbon number is y, and the carbon number is 1~ 20, Eudragityl, diethylaminemethanyl, # ° enumeration: amine methyl sulfhydryl, methyl amine substrate Mercapto group, etc., alkylthio group (preferably 132042.doc -32. 200914579 is a carbon number of 1 to 30, more preferably a mountain is 1 to U, for example, the number is 1 to 2G, especially It is good that the carbon number is 6 ^ carbon number, ethyl thio group, etc.), aryl thio group (preferably 6 士, for example, ~ can be listed as a carbon number of 6 to 2 〇, especially good Is a carbon number of 1 to 30, more preferably m, etc.), a heteroarylthio group (preferably, the carbon number is, for example, oxime, m is 1 to 20 carbon atoms, particularly preferably the carbon number is 12, sulfhydryl, ... 2::;),,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, 1 to 12, for example, may be listed as 1 to 30, more preferably a carbon number A / a rhyme group (preferably, the carbon number is, for example, methyl sub = 2 is preferably a carbon number (four), more preferably Is soil = base, etc.), serving base (the number is 1 to 12, for example, urea base, nail is good, special), scale amine (preferably / soil, base service base) ～2. Particularly preferably, the carbon number is 丨~2 such as 3°, more preferably the carbon number is amine group, phenyl sulfonamide] a diethyl fluorinated fluorine atom, a diterpenoid 1 group, a ruthenium atom (for example, a ruthenium atom, a side atom, a hard atom group, an exact group, a (tetra) acid group, a ruthenium group, a fluorenyl group, and its base 1 (The carbon number is preferably (4), more preferably an amine group or a heterocyclic group, and examples thereof include a nitrogen atom, an oxogen, and 〜12'. Examples of the pyrogen include, for example, a mercapto group, a heart, and a hydrazine. , sub, specifically, base " bottom bite base, morphinyl, benzoxene,, " fumonyl, porphinyl, etc.) m (preferably carbon number is 3~: (tetra)-based benzene It is preferable that the core is 3 to 3 Å, and it is particularly preferable that the number of carbon atoms is 3, and the carbon number is, for example, trimethyl decane 132042.doc -33 - 200914579, triphenyl decyl, etc.). These substituents may be further substituted. Specific examples of the aromatic amine derivative represented by the formula (I) of the present invention are shown below and in the synthesis examples, but are not limited to the above-exemplified compounds. [Chem. 20]

132042.doc -34- 200914579

[Chem. 21]

132042.doc -35- 200914579

[Chem. 23]

132042.doc -36- 200914579 [Chem. 24]

The aromatics of the present invention are described below. The production method of the amine derivative is said to be inferior to the method of producing the aromatic amine derivative represented by the formula (1), and is not limited to the use of the amine derivative. Pan Aroma # "One go for example: can be needle ngR4., /, Fangxiangzu _ compound' use Tetrahedron 4 〇 (1984) 1435 ~ 1456 as described in the copper charm of the battle, the copper catalyst, or Journal of The

Am_anChemicaI ί23 (2〇〇ι) 7727~ The palladium catalyst recorded by Assist is manufactured by coupling reaction. The aromatic amine derivative of the present invention is preferably used as a material for an organic EL device, and more preferably used as a light-emitting material for an organic EL device, particularly a dopant material. 132042.doc • 37- 200914579 The organic EL device of the present invention is characterized in that an organic electroluminescent device comprising an organic compound layer including at least one layer or a plurality of layers of a light-emitting layer is sandwiched between a pair of electrodes, and the organic compound layer is At least one layer contains at least one aromatic amine derivative of the present invention. In the organic ruthenium element of the present invention, it is preferred that the luminescent layer contains at least one of the above aromatic amine derivatives, and it is preferred that the luminescent layer contains 0.01 to 20% by weight of the aromatic amine derivative of the present invention. More preferably, it contains 0.5 to 20% by weight, particularly preferably 丨~2〇% by weight, and most preferably 5~20% by weight. When the aromatic amine derivative of the present invention is used as the organic material of the element (fourth material), it is preferred that the light-emitting layer contains at least one of the above aromatic (tetra) organisms and is selected from the group consisting of τ (2a) At least one of the compounds represented by the group (2d) is preferably selected from at least one of the compounds represented by the following formulas (4) to (10) as a host material. Hereinafter, the general formulae (2a) to (2d) will be described. General formula (2a) [Chem. 25]

In the formula (2a), ^ & 独立 are independently derived from an aromatic ring having a substituted or unsubstituted stone anther number of 6 to 20, and the above-mentioned square aromatic ring may be one or more. Substituents for the substitution of the above aromatic ring 132042.doc -38- 200914579 The base may be selected from substituted or unsubstituted aryl groups having a carbon number of 6 to 5 G, substituted or unsubstituted carbon number 1 to 5 院, the substituted or unsubstituted carbon group having a carbon number of 3 to 5 G, substituted or unsubstituted carbon number of pit 50, peak or unsubstituted Aromatic (the number of carbon atoms in the aryl moiety is 6 5〇', the carbon number of the alkyl group is 1 to 5), substituted or unsubstituted, having a carbon number of 6 to 50, substituted or unsubstituted a substituted or unsubstituted alkoxycarbonyl group having 6 to arylthio groups (having a carbon number of 50 in the alkoxy moiety), a substituted or unsubstituted sulfonyl group, a suspending group, and a halogen The atom, the cyano group, the nitro group and the hydroxyl group are specific examples of Rm to Rll8, and can be derived from the groups described below. When the aromatic ring is substituted by two or more substituents, the substituents may be the same or different, and the adjacent substituents may mutually form a saturated or unsaturated cyclic structure. Preferably, Arll is different from Ar. Further, at least one of Ar and Ari2 is preferably a substituent having a substituted or unsubstituted condensed ring group having a carbon number of 1 〇 to 3 Å, more preferably substituted or unsubstituted. a substituent of a naphthyl group. Examples of the group derived from an aromatic ring having 6 to 2 carbon atoms which are substituted or unsubstituted with Ar11 and Ar12 include a phenyl group, a fluorene-naphthyl group, a 2-naphthyl group, an anthracenyl group, and 2 -fluorenyl, 9-fluorenyl, phenanthrene, 2_phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthyl, 2-naphthyl, 9-naphthyl, anthracene Indenyl, 2-hydrazino, 4-indenyl, 2-biphenylyl, 3-phenylbiphenyl, 4-biphenylyl, p-triphenyl-4-yl, p-triphenyl-3-yl, coupled Triphenyl-2-yl, m-triphenyl-4-yl'-inter-triphenyl-3-yl, m-triphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, P-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 3-mercapto-2-naphthyl, 4-nonylnaphthyl, 4-fluorenyldipyridyl 132042.doc •39- 200914579 base, 4,_methylbiphenyl &, 4,, -t-butyl-tertiary triphenyl-4-yl and the like. It is a group derived from a substituted or unsubstituted aromatic ring having a nuclear number of 1 to 14 and particularly preferably a naphthyl group, a 2-naphthyl group or a phenanthryl group. R R / knife independently is selected from hydrogen atoms, substituted or unsubstituted

An aryl group having a number of 6 to 5 G, a substituted or unsubstituted heteroaryl group having a carbon number of 4 to 5 Å, a substituted or unsubstituted carbon group of the group (10), substituted or not a substituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group (the number of aryl knives is 6 〜50, the alkyl moiety has a carbon number of 50; the substituted or unsubstituted aryloxy group having 5 to 50%, substituted or unsubstituted aromatic sulphur having a carbon number of 5 to 50 a substituted or unsubstituted alkoxycarbonyl group (having a carbon number of from 1 to 50 in the alkyl moiety), a substituted or unsubstituted alkylene group, a carboxyl group, a dentate atom, a cyano group, a nitro group and a hydroxyl group. Base. The substituted or unsubstituted aryl group having a carbon number of 6 to 50 as the formula (2a) can be exemplified by a phenyl group, a fluorene-naphthyl group, a 2-naphthyl group, and an anthracene group. , 2-onion, 9-fluorenyl, phenanthryl, 2-phenanthrenyl, 3-phenanthryl, 4-phenanthrenyl, 9-phenanthryl, 1-naphthyl, 2-naphthyl, 9-naphthyl, anthracene Indenyl, 2—youji, 4—youji, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-triphenyl, p-triphenyl-3-yl, p-triphenyl-2- _ group, m-triphenyl-4-yl group, m-triphenyl group, m-triphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-tert-butylphenyl group, (2_Phenylpropyl)phenyl, 3-methyl-2-yl, 4-methyl-1-naphthyl, 4-methyl-1-indenyl, 4'-methylbiphenyl, 4 -Secondyl butyl-p-triphenyl-4-yl, 9,9-dimethylindole_ι_yl, 9,9-monomethylhydrazine-2-yl, 9,9-dimethyl- 3-based, 9,9-dimethylindole-4- 132042.doc • 40· 200914579 base. Further, it may be a substituent in which a m-phenyl group, a phenylene group, or a naphthyl 'naphthyl group is combined (for example, a phenylnaphthyl group, a naphthylphenyl group, a naphthylnaphthyl group, a naphthylnaphthylnaphthyl group) Di-T of phenylphenylnaphthyl, naphthylnaphthylphenyl, naphthylphenylnaphthyl, naphthylphenylphenyl, phenylnaphthylnaphthyl, phenylnaphthylphenyl, etc., as formula (2akR(1) The substituted or unsubstituted carbon 4 to 50 heteroaryl group of R(1) may, for example, be a (tetra)yl group, a 2-indenyl group, a phenyl group, a pyrazinyl group, a 2-pyridyl group, a 3-pyridyl group or a 4-pyridine. Base, 嗓 嗓 base, 2-mercapto group, fluorenyl group, 4, fluorenyl group, 5, silk, "inducing sulfhydryl, 7-called brodyl, sigma ten base, 2 _ different Duoji, 3_iso-decyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, : bite base, 3 ten south base, 2_benzene and bite base, 3 _Benzene and ketone base, stupid and astringent base, 5_benzoxanthyl group, 6_benzoxanyl group, 7-benzoxanthyl group, 1_iso- and stupid, Nanki, 3· Isobenzophenanyl, 4-isobenzopyrene, 5·iso-p-bromo, 6-isobenzoxanyl, 7-isobenzopyranyl, porphyrin, 3- Porphyrin 4_quinolinyl, 5-phenylindolyl, cardiopurinyl, 7-carbolinyl, 8-carbolinyl, 丨-isoindolyl, % isoindolinyl, indomethionine, 5_ Hetero (tetra)yl, 6-iso(tetra)yl, 7-iso(tetra)yl, 8_lilinyl, 2-cleavyl, 5-(tetra)-lin, b (tetra)-based, 丨10, 2-carbyl , 3_ card. Sit-base '4_ card. Sit-base, 9-carbyl, bromopyridinyl, 2-morphine, 3-morphine, p-non-bite base 6-brown base, 7 _ morphinyl, 8-cyridinyl, 9-cyridinyl, 1 啡 啡 啶 丨 丨 丨 丫 丫 丫 丫 丫 丫 丫 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 3- 定 定 定 定 定 定 定 定 定, 丨, 7-morphine_2_yl, n-morpholin-3-yl, 丨^非琳-4_yl, 丨^非琳士基, 丨, 7-phenoline j-based, 1,7-morphine琳-8-基, 啡琳_9_基, 莉琳善基, (8·132042.doc •41 - 200914579 morpholin-2-yl, 1,8-morpholin-3-yl, 1,8- Porphyrin-4-yl, 1,8-morpholin-5-yl, 1,8-morpholin-6-yl, 1,8-morpholin-7-yl, 1,8-morpholin-9-yl 1,8-morpholin-10-yl, 1,9-morpholin-2-yl, 1,9-morpholin-3-yl, 1,9-morpholin-4-yl, 1,9-morphine -5-5-yl, 1,9-morpholin-6-yl, 1,9-morpholin-7-yl, 1,9-morpholin-8-yl, 1, 9-morpholin-10-yl, 1,10-morpholin-2-yl, 1,10-morpholin-3-yl, 1,10-morpholin-4-yl, 1,10-morpholin-5 -yl, 2,9-morpholin-1-yl, 2,9-morpholin-3-yl, 2,9-morpholin-4-yl, 2,9-morpholin-5-yl, 2,9 -morpholin-6-yl, 2,9-morpholin-7-yl, 2,9-morpholin-8-yl, 2,9-morpholin-10-yl, 2,8- ° non-lin-1 -yl, 2,8-morphine-3-yl, 2,8-morphine-4-yl, 2,8-norrose-5-yl, 2,8-morpholin-6-yl, 2,8 -morpholin-7-yl, 2,8-morpholin-9-yl, 2,8-morpholin-10-yl, 2,7-morpholin-1-yl, 2,7-morpholin-3- , 2,7-morpholin-4-yl, 2,7-morpholin-5-yl, 2,7-morpholin-6-yl, 2,7-morpholin-8-yl, 2,7- ° non-lin-9-yl, 2,7-morphin-10-yl, 1-°Puzazinyl, 2-morphyl, 1-α non. Serotonyl, 2-morphinyl, 3-morphoxazinyl, 4-1#嗟π-methyl, 10-methyl-zincyl, 1-phenylpyrazine, 2-morphoxazinyl, 3-morphinyl, 4-morphyl ketone, 10 0-morphine, Qin, 2 -oxime, 4-11. Sitting base, 5-11, α sitting base, 2-11, 2nd. Sitrate, 5- to 2 aryl, 3 -Df-decyl, 2 - ° thiophenyl, 3 - ° thiophenyl, 2-mercaptopyrrol-1-yl, 2-methylpyrrole-3- , 2-methylpyrrol-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-mercaptopyrrol-4- , 3-methylpyrrole-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl) 0-bi-1-yl, 2-methyl-1 - 0 π 朵, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1_α-intro 4 - a second butyl-1-11 fluorenyl group, a 2 -t-butyl-3-α-indolyl group, a 4-tert-butyl-3-0-indolyl group, and the like. 132042.doc -42- 200914579 The substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R111 to r1 18 of the formula (2a) can be exemplified by methyl, ethyl, propyl and isopropyl groups. , n-butyl, first butyl, isobutyl, tert-butyl 'n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-isobutylidene, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-di-butyltributyl, 1,2,3-trihydroxypropyl, Gas sulfhydryl, 1-chloroethyl, 2-chloroethyl, 2-oxisobutyl, iota, 2-dichloroethyl, 1,3-diisopropyl, 2,3-digas- Tributyl, 1,2,3-trichloropropyl, bromomethyl, i_bromo

Base, 2-bromoethyl, 2-bromoisobutyl, hydrazine, 2-dibromoethyl, hydrazine, 3-dibromoisopropyl, 2,3-- > odor-tertiary butyl, 1, 2,3-tribromopropyl, iodonium, diethylidene, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 13-diiodoisopropyl, 2, 3-diiodo-tert-butyl, ^3-triiodopropyl, aminomethyl, aminoethyl, 2-aminoethyl, 2-aminoisobutyl, hydrazine, 2-diamine Ethyl, 1,3-diaminoisopropyl, 2,3-diaminotributyl, anthracene, 2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, ι,3·dicyanylisopropyl, 2,3-dicyano-tert-butyl, 1, 2,3-Tricyanopropyl, decylmethyl, 丨-nitroethyl, 2-nitroethyl, 2-stone schylyl isobutyl, i,2-dinitroethyl, u-dinitrogen Isopropyl, 2,3-dinitro-tert-butyl, anthracene, trinitropropyl, and the like. The substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms as the substituent of the formula (2a), Rm to Rm and the t-ring of the above-mentioned t group, may be exemplified by cyclopropyl, cyclobutyl and cyclopentane. Base, cyclohexyl, 4-methylcyclohexazone, benzylidene, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. The substituted or unsubstituted carbon of the formula (4) is (13) 132042.doc -43 - 200914579 alkoxy, which is a group represented by -ΟΥ, and γ is selected from the above-mentioned R1 π~Rlls Or the unsubstituted carbon number is the alkyl group of the brother. a substituted or unsubstituted aralkyl group as a substituent of R111 to R1U of the formula (2a) (the carbon number of the aryl moiety is 6 to 5 Å, and the carbon number of the alkyl moiety is 1 to 5 Å) Listed: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, ^ (α-naphthyl)ethyl, 2-(α-naphthyl)ethyl, naphthyl)isopropyl, 2-(α-naphthyl)isopropyl, β-naphthylmethyl, i_(p_naphthyl) Ethyl, 2_(0-naphthyl)ethyl, 1-(β-naphthyl)isopropyl, 2-(p-naphthyl)isopropyl, 1d bromomethyl, 2-(1-» Bioryl)ethyl, p-methylbenzyl, m-methylbenzyl, o-nonyl fluorenyl p-chloroindenyl, m-decyl, ortho-sulphur, argon, m-bromobenzyl, o-bromo Benzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, meta-amino, ortho-aminobenzyl , p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, hydrazine-hydroxy-2-benzyl isopropyl, 1- Chloro-2- Phenylisopropyl and the like. The substituted or unsubstituted aryloxy group and arylthio group of R111 to R118 of the formula (2a) of 6 to 5 are represented by -OY, and -SY", γ, and γ" are selected from The substituted or unsubstituted aryl group of the above Rln to R118 has an atomic number of 6 to 5 Å. The substituted or unsubstituted alkoxy group of R111 to R118 of the formula (2a) (the carbon number of the alkyl group is 1 to 50) is represented by -COOZ, and the Z system is selected from the above substituted R111 to R118. Or an unsubstituted carbon group having a carbon number of 1 to 5 Å. As the substituted alkylene group of R111 to R118 of the formula (2a), there may be mentioned, for example, three 132042.doc • 44 - 200914579 methyl decyl group, triethyl decyl group, tert-butyl dimethyl decyl group, vinyl group Dimethyl decyl, propyl dimethyl decyl, triphenyl decyl, and the like. Examples of the halogen atom of R111 to R118 in the formula (2a) include a fluorine atom, a chlorine atom, a bromine atom, and a dish atom. The substituents of the above R111 to R118 and/or the aromatic ring of the above Arn~AlJ2 may be further substituted by a _ atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group, an aryl group, a phenolic group, an alkoxy group or an aromatic group. Substituted by a cyclic group, an aralkyl group, an aryloxy group, an arylthio group, an alkoxycarbonyl group, a carboxyl group or the like. The anthracene derivative represented by the formula (2a) is preferably a compound having a structure represented by the following formula (2a,). [Chem. 26]

Content defined by equation (2a)

(In the formula (2a'), Ar11 and Aru and R111 to R are the same. Among them, the substituents A9 and VIII of the 9-position and the 1-position of the fluorene structure are asymmetric with respect to the XY axis.) As the organic EL of the present invention Specific examples of the derivative represented by the formula (2a) used in the element are as shown in [〇〇43] to [0063] of Japanese Patent Laid-Open Publication No. Hei. A known ruthenium derivative having two ruthenium skeletons in the molecule or a compound having one skeleton structure as shown on pages 27 to 28 of the International Publication No. 2005/061656. The representative of 132042.doc -45- 200914579 is exemplified as follows. [化27]

132042.doc •46- 200914579

132042.doc -47- 200914579 [Chem. 29]

132042.doc -48- 200914579 [化30] (

L

132042.doc 49- 200914579 [Chem. 31]

132042.doc -50- 200914579 [化32]

132042.doc -51 - 200914579

132042.doc -52- 200914579 [Chem. 34]

s·'"

Ss

•Ι?Λ

-Ι7Λ

Is

8l-il?

Bs

Ss 132042.doc -53- 200914579 [化35] ΟΛν^

SP.A S09 si

53 9n^n ffs Ψ 9i

XI 3·Μ

8i syn s74S7n 132042.doc -54- 200914579 化 ^_f\

*1-·* ΙΗ·, 4

2.S s.^ 2,3⁄4 m.ln

3**_t <m_t δ-·Λ

tcKUICKA

δ··Λ 1Β-··Τ

g •d0 42· 204 200914579 Γ

In the formula (2b), Ar13 and Ar14 are each independently a substituted or unsubstituted aryl group having a core number of 6 to 50, and L and L2 are each independently selected from a substituted or unsubstituted phenyl group. a substituted or unsubstituted naphthalenylene, a substituted or unsubstituted hydrazine group, and a substituted or unsubstituted bismuth and dibenzosilolylene group, An integer of m*〇~2, n is an integer of 卜4, s is an integer of 〇~2, and t is an integer of 0-4. Further, y or Αι_η is bonded to any position of 1 to 5 of 芘, and l2 or Aru is bonded to any position of 66~1〇. Examples of the aryl group having a core carbon number of 6 to 5 Å of Arn and Ar14 of the formula (2b) include a phenyl group, a fluorenyl-naphthyl group, a 2-naphthyl group, a K fluorenyl group, a 2-mercapto group, and a 9-fluorenyl group. , 9_ U〇-stupyl) fluorenyl, 9-(10-naphthylphenyl) fluorenyl, 9(1〇-naphthyl-2-yl) ''yl, 1-phenanthryl, 2-phenanthryl, 3 -phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthyl, 2-naphthyl, 9-naphthyl, 1-indenyl, 2-fluorenyl, 4-fluorenyl, 2-phenylidene 3_biphenyl , 4-biphenylyl, p-triphenyl-4-yl, conjugated triphenyl-3-yl, conjugated triphenyl-2-yl, m-triphenyl-4-yl, inter-linked triphenyl 3-yl, m-triphenyl-2-yl, o-tolyl, tolyl, p-tolyl, p-tert-butylphenyl, 3-methylnaphthyl, 4-methylnaphthyl' 4 —Methyl-1, fluorenyl and the like. Preferred is an aromatic ring group having a carbon number of 6 to 16 and a ruthenium group, a 1-naphthyl group, a 2-naphthyl group, a 9-(1〇-phenyl)indenyl group, and a 9-(1〇_naphthalene group). Ke-1-yl) thiol, 9-(10-naphthyl-2-yl)indenyl, 9-phenanthryl, μ, 2-yout, 4-youtyl, 2-biphenyl, 3-biphenyl Base, 'biphenyl, o-phenyl, m-tolyl, p-tolyl, p-tert-butylphenyl. Further, the above aryl group may be further substituted by a substituent, and as a substituent, 132042.doc • 56- 200914579 may be exemplified by an alkyl group (indenyl group, ethyl group, propyl group, isopropyl group, n-butyl group, second group). Base, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, I , 2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy tert-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-haloethyl, 2-chloroethyl, 2-oxisobutyl, 1,2-diethylene, 1,3-dichloroisopropyl, 2,3-digas, tert-butyl, 1,2,3-tri Gas propyl 'bromomethyl, hydrazine bromoethyl, 2-diethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3_ Dibromo-tert-butyl, 1,2,3-tribromopropyl, iodomethyl, oxime-ethyl, 2-iodoethyl, 2-iso-isobutyl, 1,2-diethyl, Im, 3_ two isopropyl, 2,3-mothane tert-butyl, 1,2,3-triiodopropyl, aminoguanidino, aminoethyl, 2-aminoethyl, 2- Aminoisobutyl, 1,2-diaminoethyl, 匕弘二Isopropyl, 2,3-diaminotributyl, iota, 2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2- Cyanoisobutyl, hydrazine, 2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-tert-butyl, 1,2,3-dicyanopropyl , nitroguanidino, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, anthracene, 3-dinitroisopropyl, 2 , 3 dinitro-t-butyl, 1,2,3-trinitropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-fluorenylcyclohexane 1, or adamantyl, 2_adamantyl, 1-norbornyl, 2-norbornyl, etc.), alkoxy having a carbon number of 丨~6 (ethoxy, methoxy, I propoxy, n-propoxy, first) a di-butoxy group, a third butoxy group, a pentyloxy group, a hexyloxy group, a cyclopentyl group, a cyclohexyloxy group, etc.), an aryl group having an atomic number of 6 to 40, and an aryl group having an atomic number of (4) Substituted amine group, - ester group having an aryl group having an atomic number of 6 to 40, an ester group having an alkyl group of 1320, 2102, doc - 57, 200914579, a cyano group, a nitro group, a halogen atom or the like. Preferably, L1 and L2 of the formula (2b) are selected from a substituted or unsubstituted phenylene group and a substituted or unsubstituted hydrazine group. The substituent is a group exemplified in the substituent of the above aryl group. The m of the formula (2b) is preferably an integer of 〇~丨. n is preferably an integer of 2 . s is preferably an integer of 〇~1. t is preferably an integer of 〇~2. Specific examples of the derivative represented by the general formula used in the organic EL device of the present invention include the asymmetry shown in [0020] to [0023] of the International Publication No. 2/5/1595. Anthraquinone derivatives. Further, a 'symmetric oxime derivative can also be used as the material for the organic EL device of the present invention. Representative examples are exemplified below. 132042.doc 58- 200914579 [Chem. 38]

132042.doc -59- 200914579 [化39]

|φ 132042.doc -60- 200914579 [化40]

132042.doc -61 - 200914579 [化41]

General formula (2c) [化42]

132042.doc • 62- 200914579 In the formula (2c), Ar15 to Ar17 are each independently selected from a group having a fluorene structure, a group having a phenanthrene structure, and a group having a fluorene structure, and Ri9 to RZ1 each independently represent a hydrogen atom or a substituent. . Ar15 to Ar17 of the formula (2c) are preferably selected from a substituted or unsubstituted nonylphenyl group, an anthracenyl group, a phenanthryl group, an 8-yl group and a phenyl group, and a good one is selected from a substituted or unsubstituted group. It is especially preferably selected from the group consisting of an anthracenyl group and a phenanthryl group. Horse type (2c)

,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, : methyl, ethyl, isopropyl, tert-butyl, n-yl, n-decyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl 2, alkenyl (preferably carbon) The number is 2 to 3 G, more preferably 2 to 20 carbon atoms, and 2 to 10 carbon atoms, and examples thereof include an ethylene group, an allyl group, a #θθ3-戍-based group, and the like. (It is preferred that the number of carbons having a carbon number of m is 2 to 20, and the number of anthrax is 2 to 1 〇, for example, a better pentyl group, etc.), an aryl group (It is preferred that the carbon number is 6 to 30, and the better the number of meteorites is 6 to 2, and the number of carbon atoms is 6 to 12, for example, the base, For f-phenyl, Hua carbon number is 〇~30, better 3/_ base "base", amine group (preferably good 疋 carbon number is 〇~2〇, especially i 0~ heart For example, an amine group, a methylamine carbon number is an amino group, a bis-amino group, a diphenylamine soil, a fluorenyl group, a diethyloxy group ( It is preferred that the carbon number is 〜2二二, -/本本胺基, etc.), and it is preferred that the carbon number is w. Further, the carbon number is ..., the oxy group, the ethyl group Examples of the hexyloxy group include an oxy group, an ethoxy group, a butyl group, and the like, and an aryloxy group (preferably, the carbon number is (i) fluorene, 132042. doc - 63 - 200914579, and more preferably the carbon number is 6 ~ 20, especially good e: stupidoxy, 1-naphthyloxy, ^ naphthalene: 弋 " carbon number is 6~12 ' For example, it can be listed as carbon number W~3G, better is the number of turns ^, etc. And a heteroaryloxy group (preferably 1 to 12, for example, pyridyloxy group: 2 2 fluorene, particularly preferably a carbon group such as a fluorenyloxy group (preferably, a methoxy group, (4) Oxygen, affinities 1 to 2. Especially good is the number of 丨 ~ heart 3 〇, more preferably the carbon number is formazan, a brewing base, triterpene ethyl ketone, etc. ^ can be cited: The base and benzene f are alkanoylcarbonyl having a carbon number of 2 to 30, more preferably (the preferred number of the slaves is 2 to 2, 2 to 2), for example, a particularly good carbon number Is a carbonyl group (preferably stone mountain soil, ethoxycarbonyl, etc.) 'Aromatic oxygen is good, the carbon number is 7~ 12, for example, can be listed: benzene's two T~I Euyl (preferably, the carbon number is 2 to 3G, and more preferably a a brewing oxygen is a carbon number of 2 to H), for example, can be listed. It is 2~2〇, especially good Rong... Lifting · Ethyloxy, Benzene oxime, and guanamine (preferably, the carbon number is 2~3: soil 2~2D, Shi, Gan w, Preferably, the inverse number of the vermiculite is benzoic acid, and the carbon number is 2 to 1 Å, for example, acetamino group, methyl group, etc., and the amine group (preferably carbon number) 2~3〇, 疋^疋wei is 2~2〇, especially good carbon number is Μ, for example, can be listed + arylamino group, etc.), if the oxetylamino group (preferably charcoal) The number is 7 to 3 Torr, more preferably the carbon number is 7 to 2 (), particularly preferably, the carbon number is 7 hearts, such as a phenoxyamino group, etc.), and the scutaneamine group is preferred. The carbon number is 1 to 3 Å, more preferably the carbon number is 2 Å, particularly preferably, the carbon number is, for example, a guanylamino group, and an amine phase group. The carbon number of the ruthenium is 0 to 30, more preferably the carbon number is 0 to 20, and particularly preferably, the carbon number is 〇~12, and for example, an amine sulfonyl group, f Aminesulfonyl, diphenyl 132042.doc -64- 200914579 amine sulphate, phenylamine yellow wine base, etc.), " 1~30, more preferably (preferably carbon number is the wilderness The number of slaves is U0, especially, for example, the amine boat I, and the carbon number of the oxime is 1 to 12, such as "amine carbamate, methylamine, phenylamine, phenylamine, etc." The base amine is a fluorenyl group, which is a charcoal Λΐ? ί) 士,甘为1~3 0, a better 疋 inverse number is 1~20, especially good carbon number thiol, ethyl thiol, etc.), 芸For example, the carbon number of the methylthio group is 6 to 3 Å, and the number of slaves is 6 to 20, and it is particularly preferable that the sputum is more. The phenylthio group is a heterocyclic thio group (preferably, the carbon number is 3 1 to 2 〇, and particularly preferably, the carbon number is 1 12 m, and the carbon number is 〜1 to 12, For example, it may be 2_benzo(tetra)thio, 2_benzoxanium] Π 咬 咬 、, 醯 ( ( (preferably ❹Γ benzo thiol), etc., its good = better carbon The number is 1~2. , especially, Α, 12, for example, may be exemplified by: gamma gg | base, etc., Aachen T sulfonyl, toluene sulfonate) sulfhydryl (preferably carbon number “ ~,, 1) 〜2〇, especially good is the number of 碳 slaves with a carbon number of t, the carbon number is (4), especially the carbon number is 12 = 3G, the more For example, the silk base and the phenyl ruthenium may be exemplified by: 1 to 3 Å, more preferably # & β phosphorus I amine group (preferably, the carbon number and the wild type of the meteorite inverse number is U0, especially For example, two or eight, the number of turns is 1 to 12, G-based sulfhydryl group, floc group, sulfhydryl group, halogenoyl group + soil private group, etc., and the hydroxyl group is atom atom (for example, fluorine atom, germanium atom, etc.) ), aryl group, μ chlorine atom, bromine group, sulfinate group, 肼Α * soil, several groups, exact groups, hydroxamic acid

30 S imido 'heterocyclic group (more than a woman's carbon number A (a) 〇, more preferably carbon (four) μ, the number of carbon atoms is a nitrogen atom, an oxygen atom, a sulfur atom, and a body atom, for example, Specifically, for example, an imidazolyl group is exemplified by 132042.doc -65 « 200914579 pyridine, quinolyl, furyl, thienyl, piperidinyl, morpholinyl, benzoxazole, benzimidazolyl, a benzothiazolyl group or the like, a decyl group (preferably, the carbon number is 3 to 4 Å, more preferably a carbon number of 3 to 30, particularly preferably a carbon number of 3 to 24, for example, a Base alkyl, triphenylsulfanyl, etc.). These substituents may be further substituted. The substituents R19 to R21 of the formula (2c) are preferably selected from the group consisting of an alkyl group and an aryl group. Expressed by the general formula (2c)

Specific examples of the c-amine derivative used in the organic EL device of the present invention,

[0079] ~ [0083] Household J derivatives. Representative examples are exemplified below. 132042.doc 66- mr 200914579 [Chem. 43]

132042.doc -67- 200914579 [Chem. 44]

General formula (2d) [化45]

Ar'*

(2d) 132042.doc -68- 200914579 A ′ 八 ～2° each independently represents an aryl group having a carbon number of 6 to 50, and the aryl group may be substituted by one or two or more substituents.

Ar~V. And at least one of the substituents of the aryl groups, and having the number H), a condensed cyclic aryl structure or a nuclear ring heteroaryl structure. ^ represents a trivalent group which is reduced by aroma. θ concentrated ring or heterozygous % derived from the formula (2d) of Ar18 ~ Ar20 imitation Shilu, up to the core of s ~ 5G aryl group carbon number is better 疋 6~30, better 6~2〇, engraved with.—# 尺6疋16. As an aryl group, a naphthyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a ketone group, a aryl group, a dentyl group, a biphenyl group, a triphenylene group, a red II 9 A group, a stupid..., a fluorescein group, a mermaid group, a fluorene group Triphenylene, benzofluorenyl. Passing the temple square can be advanced - the step has taken as the square base. The number is i 30 S. It can be enumerated: dazzle (better carbon = 30, better carbon number... especially good) The carbon number is 1 to 10, and examples thereof include methyl group, '", octyl, τ A ethyl group, isopropyl group, tert-butyl group, n-hexyl group, n-hexadecyl group, ring, etc.), a dilute base (preferably, the carbon number is 2 3 ":, "base 'cyclohexyl" anti-merma 2 to 30, more preferably the carbon number is particularly good, the carbon number is 2~] 〇m 2 butene It is 1 〇, for example, vinyl, allyl, • butyl = broad pentyl, etc.), block base (preferably, the number of good calculus is 2 to 20, especially Cup recognition 3 mountain lift: fast propyl, 3 pentyl ^ 2 ~ 1 〇 'for example, can be listed 3-pentynyl fluorene), aryl (more preferably 礴J 疋 fire number horse 6~30, read It is 6~20, especially preferably, the carbon number is 6~12. The base, the 斟甲婪婪 A _ 4 74 carbon number is 0~3〇, the second two, the base, the onion base, etc.), the amine group ( Preferably, the carbon number of the ruthenium is 0 to 20, and particularly preferably, the carbon number is 132042.doc -69·200914579 0~10', for example, An amino group, a bis-amino group, a benzyl group, a dimethylamino group, a diethyloxy group (preferably, the carbon number is 3 (;, =, didecylamino group, etc.), The best is the carbon number is ~~〗 〇, for example, the carbon number is 1~2〇, the oxy group, the & hexyloxy group, etc.; ^: methoxy, ethoxy, butyl is better The carbon number is 6 ^ fluorenyl (preferably, the carbon number is 6 to 30, and the number of phlegm is 6 to 20, and particularly preferably: phenoxy, naphthyloxy, and 2 to 6 to 12, for example, The column is the number of breaks (four), and more preferably the money is =, especially hetero-oxyl (preferably, for example, _oxy group, ratio = it = cut number is *oxy group, etc.), brewing base (It is preferred that the carbon number is a dibasic or two base group, and the ruthenium is particularly preferably a number of breaks; if the number of columns is a fluorenyl group, a fluorenyl group, a bis-ethyl ketone group, and the benzene is a carbon number 2, and more (4) is a better 2~12 of mi. For example, a good 疋 carbon number is 丞 丞 、 、 、 、 、 、 、 、 ( ( ( ( ( ( ( ( ( ( ( ( ( Good soil, aromatic sulfur, its carbon number is 7~12, 仞&, 疋 slave number is 7~20, Yuji (preferably carbon number is 2~3 f can be listed Phenoxy group, etc., brewing oxygen oxime is a few horses 2 to 30, more preferably, the carbon number is 2 to 10, for example, 2 to 2 Å, especially good, etc.), guanamine group (preferably) It is 2 to 20, especially preferably, the carbon number Y is better, and the number of sputum is benzoguanamine, etc.), and the oxygenated oxymethane: as exemplified by: acetamino group, rolling base amino group (cf. Preferably, the carbon number is 2 to more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2 3 fluorene, a methoxycarbonylamino group, etc., and an aryloxy group of 4 to 12'. Columns 7 to 30, more preferably, the carbon number is 7 to 2 Å/^^ (preferably, the carbon number is particularly preferably a carbon number of 7 to 12, for example 132042.doc -70-200914579 (10) column = An oxyamino group, etc.), a continuous amine group (preferably, the number of carbon atoms is, for example, 1 m is a number of turns of 12, for example, a carbon number αΓ, a benzene hetero group, etc.), Feed base (good number two). ~3. More preferably, the carbon number is 0 to 20, and particularly preferably the carbon number '乂 - for example, an amine sulfonyl group, a methylamine sulfonyl fluorenyl group, a phenylamine sulfonyl group, etc.), an amine A thiol group (preferably, the carbon core is as good as a carbon number of 1 to 2 Å, particularly preferably a carbon number of Η2, such as phenyl meamine amide amine, methylamine ketone , diethylamine methyl sulfhydryl, fluorenyl, etc., sulfur-based (preferably, the money is (four), more:: number: 1 to 2 °, particularly preferably, the carbon number is Η2, for example, A two: number B: base, etc.), arylthio group (preferably, the carbon number is (1)., a better number is 6 to 20, particularly preferably a carbon number of 6 to 12, for example, a benzene furnace Second,: its aromatic: the base (four) is a carbon number of 1~ 2-benzoxylthio group, such as: base, carbon number is 1~3G, better mw, and 'the meteorites are 1 to 12, for example, can be mentioned as: 碏醯美美... A benzopyrene 廿疋 carbon number is 1 to 12, for example, methyl myanthene: base sulfhydryl group, urea group (better) More: Yes:: (10) Especially good is the carbon number - for example, can be listed. Lifting: base, methylurea, phenylureido, etc.), phosphoniumamine The number is preferably 1 to 3°, more preferably the carbon number is particularly preferably the carbon number: Γ: Λ is as follows: diethylphosphonium amide, stupyl phosphonium amide, etc.) 132042.doc -71- 200914579 A dicentric atom (for example, a fluorine atom, a chlorine atom, a sulfhydryl group, a fluorenyl group, an imine group 1: (4) an acid group, a hydrazone 30, more preferably a carbon number It is a ring group (preferably, the carbon number is a nitrogen atom, an oxygen atom, or a sulfur 2 as a hetero atom, and examples thereof include a pyridine group and a quinolyl group), and specifically, for example, a mercapto group. , oxazolyl,: D soil, thienyl, piperidinyl, morpholinyl, stupid base ... m. sitting, stupid and sputum base, card recharge), dream base (better ▲ 1 Miscellaneous 3, particularly preferably a carbon number of 3 24 is more preferably a carbon number of Ά _ 4, number 24, for example, trimethyl sulfonyl group f), etc. These substituents can be further advanced It is replaced by one: ΓΑΓ~Ar2° and the substituents of the aryl groups. The naphthalene structure, the onion structure, and the aryl structure can be listed as the structure of the green, the structure of the onion, and the structure of the structure. Structure, etc. The fragrant L: knot::" It is better that the phenotype is particularly good for the ruthenium structure. As the substituent of the formula (2d), Ar18~ArM and the nucleus of the nucleus啥:啥琳-structure: The condensed ring heteroaryl structure can be listed as follows:: ΓΓ structure, (4) structure, structure, morphine structure, 啥 (4) surname structure, etc. 'Better is the structure of 啥琳, 嗤 嗤a quinoxaline, a structure, a pyridazine structure, a phenanthroline structure. The aromatic content of the Ar of the general formula (2d) is 6 to 30, more preferably 6 to 2/ of a trivalent carbon. The number is preferably 20'. More preferably, the carbon number is 6 „, which can be exemplified by benzene, naphthalene, onion, and .... Specifically, the trivalent base and the like. 132042.doc 72- 200914579 derived from the benzene derivative of the general formula (4), the trivalent group derived from Ar is preferably selected from the group consisting of atoms, sulfur atoms, and oxygen. The atom in the atom acts as a hetero atom, and more preferably contains a nitrogen atom. Further, the carbon number of the 垓3 valence group is preferably 2 to 3 Å, more preferably 3 to 2 Å, and even more preferably 3 to 16. Specifically, it may be a trivalent group derived from a predetermined tb Qin "Saichuan, Yulin, Yulin, and Sanyu. A trivalent group derived from the aromatic ring or the heteroaryl ring may be used. The substituent may, for example, be a group represented by a substituent of the aryl group of the substituent A, etc. Ar is preferably a benzenetriyl group, a naphthalenetriyl group, a diphenyl group-based group, or a combination. a trivalent group derived from diphenylene, more preferably a benzenetriyl group, more preferably an unsubstituted (Ar 8 , Arls and A2G substituted) benzenetrienyl group, an alkyl substituted benzotriyl group The specific example of the benzene derivative represented by the second sentence of the organic EL device of the present invention is exemplified by Japanese Patent Laid-Open Publication No. Hei. No. 2 324678 [0079] to [〇〇83]. Various benzene derivatives, such as the benzene derivatives shown, are exemplified, and representative examples thereof are as follows. 132042.doc 73- 200914579 [Chem. 46]

132042.doc 74- 200914579 [Chem. 47]

a

132042.doc •75- 200914579 [Chem. 48]

In the present month, as an organic thin film in which the organic film is a plurality of layers, a laminate (anode/cavity implant layer/light emitting layer/cathode), (anode/light emitting layer/electron implant layer/cathode) can be cited. ), (anode / hole implant layer / light-emitting layer / electronic implant layer / cathode) and other structures. In the above plurality of layers, "other than the aromatic amine derivative of the present invention may be used as needed", a well-known luminescent material, a doping material, a hole-laying material or an electronic planting material may be further used. The organic EL element can prevent a decrease in brightness or lifetime due to the quenching of the organic thin film layer by making the above-mentioned organic thin film layer into a plurality of layers. If necessary, a combination of luminescent materials, rework, hole-laying materials or electronic implant materials can be used. Also, too. The doping material is used to increase the illuminating brightness or the illuminating efficiency, and emit red or = light: In addition, the hole arranging layer, the illuminating layer and the electron arranging layer can respectively form a layer structure of two or more layers. At this time, in the case of the electric hole implant layer, the layer from the electrode implanted hole is called the electric hole implant layer, and the layer from the electric hole is implanted and the hole is transported to the layer of the light-emitting layer. In the case of a hole in the electron tunneling layer, the layer from which the electrode is implanted is called an electron implant layer' and receives electrons from the electron implant layer and turns the electrons into the light-emitting layer. The layer is called an electron transport layer. These layers can be selected for use depending on the adhesion of the material to the organic layer or the metal electrode. The host material or the doping material other than the above formula (2a) to (2d) which can be used together with the aryl (tetra)amine derivative of the present invention for the light-emitting layer, for example, naphthalene, phenanthrene, red fluorite, Onion, thick tetraphenyl m, ten production, such as 'tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, first, snail second:: diphenyl onion, 9 count double (phenylethyl fast ... 静乙块基心土) This special condensation more than aromatic compounds and these derivatives, Shao, bis (2_ fluorenyl -8, yl (tetra) phenyl benzene purchased complex 'triarylamine derived Benzene amine derivative, :: acetamidine derivative 'coumarin derivative', "pyran derivative", "four" derivative, stupid and hydrazine derivative, benzoxanthene derivative, benzene a hydrazine derivative " a bisulidine derivative, a cinnamic acid derivative, a bismuthine derivative, a ketone ketone derivative, a quinone ketone derivative, etc., but is not limited thereto 132042.doc -77- 200914579, etc. As a hole-laying material, it is preferable to have the ability to transport holes, and have a self-anodizing cloth (4). The compound light-emitting layer or light-emitting The effect of Yuli (5) and the effect of 洞1: hole planting, the generated exciton has excellent forming ability to the electron implant layer or the luminescent layer film. I body ^ π planting (4) moving, and thin η list:駄菁街生物,Naphthalene: He bio, derivative,,,,,,,,,,,,,,,,, Knee, polyaryl fumed tobacco, diphenylethylene m, nitrile triphenylamine, styrene amine trisuccinylamine, diamine triphenylamine, and the like, and polyethylene A polymer material such as a card, a polyvalent or a conductive polymer is not limited thereto. It can be used in the hole-laying material of the organic hole element of the present invention, and the more effective hole-laying material is a family of materials. a tertiary amine derivative and a μ derivative. As an aromatic tertiary amine derivative, for example, there are triphenylamine, tricresylamine, tolyldiphenylamine, hydrazine, hydrazine, _diphenyl hydrazine, hydrazine, _(3_methylphenyl)_biphenyl-4,4,-diamine 'Ν,Ν,Ν,,Ν,·(4_methylphenyl)", broad phenyl _ 4, 仏二Amine, hydrazine, hydrazine, hydrazine, hydrazine, _( 4-methylphenylbiphenyl-4,4,diamine, anthracene, anthracene, -diphenyl-fluorene, anthracene, -naphthyldecylbiphenyl-4-4,4,diamine, anthracene ,Ν'-(methylphenyl)-oxime, hydrazine, _(4_n-butylphenyl)phenanthrene-9,1 〇diamine, hydrazine, hydrazine bis (4-di-4-methylamino) Phenyl)- 4-phenylcyclohexane or the like, or an oligomer or polymer having the mono-amine's secondary amine skeleton, but is not limited thereto. As a phthalocyanine (Pc) derivative For example: h2Pc, CuPc, CoPc, 132042.doc -78- 200914579

NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ciGaPc, CllnPc, CISnPc, Cl2SiPc, (H0)A1PC, (H0)GaPc, VOPc, TiOPc 'MoOPc, GaPC-O-GaPc, etc. Phthalocyanine derivatives and Chuaphthalocyanine derivatives , but not limited to these. Further, in the organic EL device of the present invention, it is preferred to form a layer containing the aromatic tertiary amine derivative and/or a phthalocyanine derivative between the light-emitting layer and the anode, for example, the above-mentioned hole transport layer or hole. Planting layer. As the electron-carrying material, it is preferable that the compound has the ability to transport electrons and has an effect of implanting electrons from the cathode and an excellent electron-distributing effect on the light-emitting layer or the light-emitting material, thereby preventing the light-emitting layer. The generated excitons move toward the hole implant layer, and the film forming ability is excellent. Specific examples include ketone, decane, biphenyl fluorene, dioxin, p-number 0, p-type di-p-, and tri-. Sit, mites, flowers, tetracarboxylic acid, sulfhydryl methane, quinodimethane, fluorenone, and the like, but are not limited thereto. Further, sensitization can be carried out by adding an electron-withdrawing substance to the hole-implanting material and adding an electron-donating substance to the electron-carrying material. Among the organic EL devices of the present invention, more effective electronic implant materials are metal complex compounds and nitrogen-containing five-membered ring derivatives. Examples of the metal complex compound include lithium quinolate, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, and the like. (8-hydroxyquinoline) aluminum, tris(2_hanyl-8-hydroxyquinoline)aluminum, tris(8 via kiline) gallium, bis(1〇_p-benzobenzo[匕]啥琳)铍, bis(1〇carboxybenzo[h]quinoline), bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline) (o-cresol) gallium, Bis(2-methylquinoline) (naphthol) aluminum, bis (2_methyl 132042.doc • 79-200914579 -8-quinoline) (2-naphthol) gallium, etc., but is not limited thereto Wait. As the above nitrogen-containing five-membered derivative, for example, oxazole, thiazole, % monoazole, thiadiazole, and triazole derivative are preferred. Specifically, 2,5-bis(1-phenyl)-1,3,4-carbazole, dimethyl p〇p〇p, 2,5-bis(1phenyl)_ 1, 3,4 塞塞,2,5_double (1_phenyl hap oxadiazole, 2_(4,_t-butylphenyl)-5-(4")biphenyl)-13,44 Azole, 2,5-bis(i-naphthyl)_13,4_%-azole, 1,4-bis[2-(5-phenyloxadiazolyl)]benzene, M-bis[2_(5-phenyl Can sit a base)-4-t-butylbenzene], 2_(4,_t-butylphenyl)·5_(4,,_biphenyl)_1,3,4-anthraquinone, 2, 5·bis 0-naphthyl)-1,3,4-thiadiazole, 1,4-bis[(5phenyl sulphide)]benzene, 2_(4,_third phenylene linkage Phenyl)-1,3,4_triazole, 2,5-bis(naphthyl)·1,3,4-triazole, Μ_bis[2_(5-phenyldiazolyl)]benzene, etc., but is not limited thereto Wait. In the organic EL of the present invention, the light-emitting layer may contain at least one selected from the group consisting of amine derivatives represented by the formula (1), and in the same layer: 3 has a calendering material, a doping material, The electric hole planting material and the electronic cloth material; the seed is further improved in temperature, humidity, environment, etc. by the organic EL element obtained by the present invention, or a protective layer may be provided on the surface of the element, or Oil, resin, etc. protect the entire component. As the anode (four) f-material used in the present invention, a work function greater than 4 eV can be applied, and carbon, Shao, 鈒, iron, start, record, pseudo, silver, gold, face, and the like can be used and these The alloy is used for the tin oxide, indium oxide, etc. of the NESA substrate, and can be used for the conductive conductivity of the cathode from the land F, or the organic conductivity w such as polypyrrole. If the work function is less than 4 eV, you can use magnesium, calcium, tin, 132042.doc 200914579, titanium, Ji, Jing, Yi, Meng, Ming, gasification, etc. and these alloys, but Not limited to these. Examples of the alloy include ruthenium, town/indium, and fun/aluminum, and the like, but are not limited thereto. The ratio of the alloy can be controlled by the temperature, environment, degree of vacuum, etc. of the source, and the ratio is selected: the appropriate ratio. The anode and the cathode can form a layer structure of two or more layers if necessary. In the organic EL device of the present invention, at least one of the surfaces is sufficiently transparent in the light-emitting wavelength region of the device. It is preferable that the substrate is also transparent. The transparent electrode is made of the above-mentioned conductive material, and is set so that specific light transmittance can be ensured by a method such as vapor deposition or sputtering. The light projection rate of the electrode of the light-emitting surface is preferably 1% or more. The substrate is not limited as long as it has mechanical and thermal strength and transparency, and has a glass substrate and a transparent resin film. Examples of the transparent resin film include polyethylene, ethylene-vinyl acetate copolymer, ethylene vinyl alcohol copolymer, polypropylene, polystyrene, polymethacrylic acid brewing, polystyrene, and polyhexenol. , polyvinyl butyral, nylon, polyetheretherketone, polyfluorene, polyether oxime, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-b: copolymer, tetrafluoroethylene Rare-hexafluoropropane copolymer, polychlorotrifluoroethylene, polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimine, polyetherimide, poly Amine, polypropylene, etc. The formation of each layer of the organic EL device of the present invention may be carried out by a dry film formation method such as vacuum distillation, sputtering, plasma, or ion ore, or a wet film formation method such as dip coating or flow coating. a way. The film thickness is not particularly limited, but it is necessary to set it to an appropriate film thickness. If the film thickness is too thick, the efficiency is deteriorated in order to obtain a fixed light rotation. If the film thickness is too thin, pinholes and the like are generated at 132042.doc -81 - 200914579, and even if the degree of repellent is applied. The usual mode thickness of the film - the first hair of the brother knife nm ~ f) 9 ^ target range of 5 nm ~ 10 _, more preferably 10 nm 0 · 2 μηη range. In the case of the wet film formation method, the material of each layer is dissolved or formed into a suitable solvent such as melamine or dioxane to form 4 films, and the solvent may be any solvent. . As the solution suitable for such a wet preparation, a solution containing the present invention: a scented aromatic amine derivative and a solvent as an organic anal material can be used. Further, the organic EL material includes a host material and a dopant material. The dopant material is an aromatic amine derivative of the present invention, and the host material is selected from the group consisting of the formula (2a), the formula (2b), and the formula. (10) and at least one of the compounds represented by the formula (IV). Further, in any of the organic thin film layers, in order to improve film formability and prevent pinholes or the like from being formed on the film, an appropriate resin or additive may be used. Examples of the usable resin include polystyrene, polycarbonate, polyarylate, polyester, polyamine, polyurethane, polysulfone, polymethyl methacrylate, and polymethyl acrylate. An insulating resin such as cellulose or a copolymer thereof, a photoconductive resin such as poly-N-vinylcarbazole or polydecane, or a conductive resin such as polythiophene or polypyrrole. Further, examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer. The organic EL device of the present invention can be used for a flat illuminator such as a flat panel display for a flat panel television, a backlight for a photocopier, a printer, a backlight for a liquid crystal display, or a light source such as a leaf device, a display panel, a marker lamp, or the like. Further, the material of the present invention 132042.doc -82- 200914579 can be used not only for an organic EL element but also for an electrophotographic photoreceptor, a photoelectric conversion element, a solar cell, an image sensor, and the like. EXAMPLES Hereinafter, the present invention will be described in detail using Synthesis Examples and Examples. The synthetic steps of the compounds D-41 to D-54 synthesized in the synthesis examples are shown below. [化 49] «12 αιιΗ#^φ

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Ja-D 9ζ5Ηί®4-丨5V5V ^OVOJPd a ,Λ Synthesis Example 1: Synthesis of D-41 Synthesis Example (1-1): To a 500 mL eggplant-shaped flask, 14.2 g of trifluoromethanesulfonic acid 6- was added. Bromo-2-naphthyl ester, 8.0 g of trans-2-(4-phenylphenyl)vinylboronic acid, 1.4 g of Pd(PPh3)4, 12.8 g of sodium carbonate (clean water 60 mL), and toluene, 132042 .doc -86- 200914579 The reaction was carried out under reflux for 8 hours under a stream of argon. After cooling, the reaction solution was filtered, and the obtained solid was washed with clean water and methanol. The obtained crude product was dissolved in hot toluene and purified by silica gel chromatography (toluene), and the obtained solid was dried under reduced pressure to give 6.6 g of a white solid. It was identified as an intermediate by FD-MS (field desorption mass spectrometry, field desorpti〇n-mass spectrum). Synthesis Example (1-2): To a 3 mL mL eggplant-shaped flask, 6.6 g of an intermediate j, 26 〇 mgiPd (〇Ac) 2, and 3 7 Å were added under a stream of argon gas, and the reaction was carried out for 8 hours. After cooling, the reaction solution was passed through, and the obtained solid was washed with clean water and methanol. The obtained crude product was dissolved in hot toluene to be purified by gel chromatography (toluene), and the obtained solid was recrystallized twice (benzene), and the solid obtained by washing with normal hexane was decompressed. Drying gave the result as a yellow solid. Using FD-MS analysis, it was identified as d_4i. Synthesis Example 2: Synthesis of D-42 In Synthesis Example (1-1), 2,6·diin 4,S-monomethylnaphthalene was used instead of 6-bromo-2-naphthyl trifluoromethanesulfonate. In the same way

Friends retired and synthesized. It was identified as Intermediate 2 by analysis of FD-MS. In the synthesis example (1_2), the intermediate 2 was used instead of the intermediate, and bis(β-naphthyl)amine was used instead of diphenylamine.

FnM<^八& t lost the square to go into the synthesis. It was identified as 〇_42 by FD-MS. Synthesis Example 3: Synthesis of D-43 In Synthesis Example (1-1), 2,6_-filled with '4,8-diphenylnaphthalene was used instead of trifluoro 132042.doc-87-200914579 formosin 6- Bromo-2-naphthyl vinegar was synthesized in the same manner. It was identified as Intermediate 3 by analysis of FI·. In Synthesis Example )-2), an intermediate 1 2 3 4 was used instead of the inter alia, and bis(3,5-dimethylphenyl)amine was used instead of diphenylamine, and the synthesis was carried out in the same manner. Using the analysis of FD-MS, it was identified as D_43. Synthesis Example 4: Synthesis of D-44 In Synthesis Example (1-1), '3,7-dibromo-, one-formed furan was used instead of trifluoromethyl 6 hexa-2-naphthalene 8' was carried out in the same manner. synthesis. It was analyzed by the analysis of MS to identify it as intermediate 4. In the synthesis example (1-2), the intermediate 4 was used instead of the intermediate i, and the synthesis was carried out in the same manner. The analysis of Li De (field desorption mass spectrometry) was D-44. Synthesis Example 5: Synthesis of D-45 In Synthesis Example (1_1), 丨4_二淳果奈 was used instead of trifluoromethanesulfonic acid 6-bromo---S曰, and the synthesis was carried out in the same manner. It is designated as intermediate 5. In the analysis of her D-MS, in the case of Example (4), intermediate 5 was used instead of the intermediate], and two ethyl phenylamines were used instead of diphenylamine in the same manner. to make. Using FD-MS analysis, it was identified as d_45. Synthesis Example 6: Synthesis of D-46: (in the case of '1_υ中', using 2,8, 2, and diphenyl hydrazine instead of tris-methyl-88 - 1 as described in the same method. Knife analysis, identified as intermediate 6. 3 In the case of (1-2), intermediate 6 was used instead of intermediate i, and biphenyl 4 132042.doc 200914579 phenylamine was used instead of diphenylamine. The method was synthesized. It was identified as D-46 by FD-MS analysis. Synthesis Example 7: Synthesis of D-47 (2-1): Under a stream of argon, add 1000_0 to a 1000 mL eggplant-shaped flask. g 6-bromo-2-naphthyl triflate, 5.5 g of [1, bis-bis(diphenylphosphino)ferrocene] palladium di-palladium, 11.7 g of lithium bromide, and dehydrated THF, cooled to Add 135 mL of methylmagnesium bromide in THF (1 mol/L) at -20 ° C, slowly heat up, react at room temperature for 2 hours, and react at 80 ° C for 4 hours. After cooling, add 10 The aqueous solution of hydrochloric acid and hydrazine were separated, and the organic layer was washed with sodium bicarbonate solution and saturated brine, dried over magnesium sulfate, and concentrated by silica gel chromatography (di-methane, hexane). The product was purified and the solid obtained was purified by silica gel chromatography (hexane). The obtained solid was dried under reduced pressure to give 15 g of a white solid, which was identified as an intermediate by FD-MS analysis. 7. Synthesis Example (2-2): In a 300 mL eggplant-shaped flask, 15.0 g of Intermediate 7, 12.1 g of N-bromosuccinimide, 1 〇〇mg of azobispyrene was added under a stream of argon gas. The nitrile and the carbonized carbon are reacted under reflux for 3 hours. After cooling, the clean water and the methane are added, and the liquid is separated and extracted. The organic layer is washed with water/saturated brine and dried with sodium sulfate. The crude product obtained by concentration was purified by silica gel chromatography (dioxane, hexane), and the obtained solid was dried under reduced pressure to obtain 16.2 g of a white solid, which was identified by FD-MS analysis. For the intermediate 8. Synthesis Example (2-3): Under a stream of argon, into a 300 mL eggplant-shaped flask, add 16.0 g of intermediate 8, 14 g of triethyl phosphite, heat up, distill, and go to 132042.doc -89- 200914579 After removing the ethyl bromide formed, it is distilled under reduced pressure to remove unreacted Triethyl phosphate obtained 19.2 g of a white solid. It was identified by FD-MS (Field Desorption Mass Spectrometry) to be Intermediate 9. Synthesis Example (2-4): 1 〇〇〇 mL of cigar under argon flow In a flask, add 30.0 g of 1,4-dibromonaphthalene, 300 mL of dehydrated THF, and cool to -65X: after adding '72 mL of n-butyl hexanol solution (1.6 Μ), react for 30 minutes, add dropwise After 25 mL of dehydrated hydrazine and hydrazine-dimethyl decylamine, the temperature was slowly raised and reacted at room temperature for 4 hours. After adding 4 Ν hydrochloric acid and toluene, and separating and extracting, the organic layer was washed with clean water and saturated brine, dried over sodium sulfate, and the crude product obtained by concentration by chromatography (toluene) was purified. The solid was dried under reduced pressure to give 20 g of white solid. It was identified as Intermediate 10 by analysis of FD-MS. Synthesis Example (2-5): In a 5 mL mL eggplant-shaped flask under argon flow, 7.1 g of Intermediate 9, 4.7 g of Intermediate 1 hydrazine, dehydrated THF, and cooled to -50 C ', 2.5 g were added. Potassium tert-butoxide was slowly warmed to room temperature and reacted for 7 hours. The reaction solution was filtered, and the obtained solid was washed with purified water and methanol, and dried under reduced pressure to give 10.8 g of white solid. It was identified as Intermediate 11 by analysis by FD-MS. In the case of Yuqi (1·2), the intermediate 11 was used instead of the intermediate 1, and the synthesis was carried out in the same manner. Using FD-MS analysis, it was identified as d-47. Synthesis Example 8: Synthesis of D-48 In Synthesis Example (2-1), 3,7-dibenzofuran was used instead of trifluoromethanesulfonic acid 132042.doc-90-200914579. Using FD-MS to divide 6-bromo-2-naphthyl ester, to precipitate, to determine it as intermediate 12 in the mouth of the example (2-2), using intermediate 12 instead of intermediate 7, in the same way Synthetic J mouth. Using FD-MS analysis, it was identified as an intermediate 13 ° in the mouth of the example (2-3), and the intermediate 13 was used instead of the intermediate 8, and the same method was used to carry out the combination of the ancient and the sigma. By FD-MS analysis, it was identified as an intermediate 14 ° \Example (25), and Intermediate 14 was used instead of Intermediate 9, and the synthesis was carried out in the same manner. Using the analysis of fd_ms, it was determined to be an intermediate 15 ° in Synthesis Example )-2), and Intermediate 15 was used instead of Intermediate 1, and the synthesis was carried out in the same manner. Using FD_MS analysis, it was identified as H synthesis Example 9: Synthesis of D-49 in the synthesis example (2·υ中中中的中的中的's use 2_漠_7_蛾_9,9_dimethylfluoromethanesulfonic acid 6-bromo _2-Extracted ester, & η Μ f $ instead of one... The same method was used for the synthesis. It was identified as an intermediate by the analysis of FD-MS. 6. In the case of Example (II), intermediate 16 was used instead of the intermediate. 7 Γ7仃Synthesis."Use FD-MS to analyze the intermediate intermediate 8 and synthesize it in the same manner as in Synthesis Example (2-3) using Intermediate 17 instead of FD-MS. Dividing ti 8 . , Zhong Ding as the intermediate dibromo naphthalene, in the synthesis example (2-4), using 4, 4, _ two filling stupid instead of 1 〆 132042.doc -91 - 200914579 in the same way The input is 仃δ成. Using the analysis of FD_MS, the inter-body is 19. 疋/, is medium

In the synthesis examples (2 to 5) φ , # M , the intermediate 18 was used instead of the intermediate 9, and the interstitial 19 was used instead of the inter- τ inter-body 10 in the intermediate production, and the synthesis was carried out in the same manner. Analysis of MS, Zhong Dingzhi as intermediate 2〇. FD- was synthesized in the synthesis example (W, using Intermediate 20 instead of the intermediate b. The sample 1 was analyzed by FD_MS and identified as D-49. Synthesis Example 10: Synthesis of D-50 in Synthesis Example ( 2-5) In the middle of the 'intermediate' instead of the intermediate compartment 19 instead of the intermediate 1 Λ using the intermediate 1 〇, the synthesis was carried out in the same way. Using Fd MS analysis, it was used as an intermediate & In the example (1-2), the intermediate p21 was used instead of the intermediate peptone, and the synthesis was carried out by the method. The analysis of MS was carried out by using fD_ms J to identify it as d_5〇. Synthesis Example 11: Synthesis of D-51

In U 2nd, '3' is used instead of 3, 7. Erdi, and the same method is used for synthesis. It was identified as intermediate 22 by analysis of fdms. ^Synthesis Example (2), using Intermediate 18 instead of Intermediate 22 instead of Intermediate 1 〇, and analyzing it in the same manner, and identifying it as an intermediate... I. Li (4) _ in Synthesis Example (1-2), The synthesis was carried out by using the intermediate 23 instead of the method. The same procedure was carried out by the FD-MS, and the synthesis of the compound 12··D_52 was carried out by the FD-MS. Synthesis Example (3-1): 2,8- Likou 8 13 · 04 132042.doc -92- 200914579 =^1 二diphenylamine, °18°-sodium butoxide, and 700 ml of xylene , and the mixture is slowly added dropwise with 32ml of three: Ding... 丨 拌 拌 拌 々 丁基 丁基 l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l The reaction was carried out for 7 hours. 3,23 g of the white color was obtained by liquid separation treatment and column chromatography. The FD_MS analysis was used to identify the intermediate as an intermediate 24 ° ( 3-2): In the !B four-necked flask, the intermediate 24 obtained by ι〇·23 § was charged, and the pressure was reduced three times and the pressure was reversed by nitrogen to replace the inside of the system with helium. Then, 3 was added. 〇〇 m l After dehydrating tetrahydrofuran, stir it, use a dry ice/acetone bath, cool to _65. About 〇, add rrU dehydrated dimethylformamide dropwise at about 5%, continue to react for 2 hours at _6r (: To the room temperature, the reaction was carried out for 2 hours, and after the mixture was stopped for n (four) hours, U)0 N hydrochloric acid was added, and then the reaction mixture was extracted with ethyl acetate/water, and the obtained organic layer was concentrated to obtain 83 g of intermediate white solid. Using FD-MS analysis, it was identified as intermediate 25. Synthesis Example (3-3): To a 500-mil three-necked flask, 2 73 g of zinc and 150 ml of dehydrated tetrahydrofuran were added while the reaction vessel was placed in an ice bath. After cooling, - 2.34 ml of titanium tetra-titanate, u. 4 ml of pyridine, and stirring with a stirrer were added dropwise. Next, 3.27 g of the intermediate 25 was dissolved in 1 Torr to dehydrate the tetrahydrogen. After the dropwise addition, the reaction solution was allowed to stand in a nitrogen atmosphere, reacted at room temperature for 20 minutes, reacted at 6 ° C for 5 hours, and added with 10% potassium carbonate aqueous solution for 5 times by liquid separation. Treatment, column chromatography purification, to obtain 1.04 g of yellow-white solid. Analysis by FD_MS Forging 132042.doc -93- 200914579 designated D-52. Synthesis Example 13: Synthesis of D-53 in Synthesis Example (3·1)+, using 3,7 Dibenzofuran, and -benfuran instead 2,8-Eight-South is analyzed by the method of the sample, and it is identified as the intermediate 26. Ding Koucheng. Using the coffee (10) in the synthesis example (3-2), the intermediate of the square is used. - Person a replaces intermediate 24 and proceeds to the same synthesis. Use fd_Ms 27. Knife analysis 'Zhong Dingzhi as an intermediate ==) in the middle of the use of the intermediate Zhao 27 instead of the _5 sample using FD-MS analysis, Zhong Dingzhi (4). . Example 14: Synthesis of D-54 in Synthesis Example (3-1), using 2,8•2.. +, one open thiophene instead of 2,8-two off one open 吱 以' in the same way Fight, I β back to Q. It was identified as Intermediate 28 by FD-MS. In the synthesis example (3-2), the intermediate 28 was used instead of the intermediate ... and the synthesis was carried out in the same manner. By the analysis of FD_MS, it was determined to be an intermediate. In the synthesis example (3·3), the intermediate 29 was used instead of the intermediate, and the synthesis was carried out in the same manner. Using the analysis of FD_MS, it is determined to be Μ. Example 1 On a scaled substrate of 25 mm x 75 mm, a film = 120 nm transparent electrode containing indium tin oxide was placed. The transparent electrode can function as an anode. Then, the glass substrate was irradiated with ultraviolet rays and ozone, and after bonding and cleaning, the substrate was placed on a vacuum deposition apparatus. 132042.doc -94- 200914579 百先,将N',N"-双[4彳-:3⁄4甘甘甘(- Benzylamino)phenyl]-ni,n"-diphenyl-based base- The 4,4'-diamine is evaporated to a thickness of ^ ^ and is 60 nm, and is used as a hole layer.

Stupid, on it, N, N, N tetrakis (4-biphenyl)-4,4,-benzidine was evaporated to n! 20 nm as a hole transport layer. Then, as the main material 4~, the birthday material (2a_1) and the aromatic amine derivative (D-4) as a doping material, the mass ratio is 4 〇: 2 A luminescent layer with a thickness of 40 nm. The thickness of the tri-(tetra)-based (iv) ore is Μη. on the luminescent layer as an electronic implant layer. - The person casts the Dunhua clock to a thickness of i nm, and then evaporates the ore to a thickness of 150 nm to produce an organic EL element. Further, the aluminum/lithium fluoride can function as a cathode. The organic EL device thus known was measured for device performance (light-emitting luminance) at a current density of 10 mA/cm 2 and a half-life at an initial luminance of 100 cd/cm 2 . The results are shown in Table 1. (Examples 2 to 15) In the same manner as in Example 1, an aromatic amine derivative represented by the above Tables to Table 3 was used instead of the aromatic amine derivative (D_44) to prepare an organic EL device. Evaluation, the results are shown in the table. Examples 16 and 17 show that in the first embodiment, the compound shown in the fourth table was used instead of the anthracene derivative (2a-1) to prepare an organic EL element, and the same evaluation as in Example 1 was carried out, and the results are shown in the table. in. Comparative Example 1 to 3 132042.doc -95- 200914579 In the first embodiment, an organic EL device was produced by selecting a compound shown below in place of the compound of the aromatic amine derivative (D-44) according to the fourth table. The same evaluation as in Example 1 was carried out. The results are shown in the table. [化53]

[Table 1] Table 1 Example 1 Example 2 Example 3 Example 4 Example 5 Host material 2a-1 2a-1 2a-1 2a-1 2a-1 Doping material D-44 D-45 D- 42 D-49 D-36 Driving voltage (V) 6.0 1 6.0 6.0 6.0 6.0 Luminous blue blue blue blue blue Luminous brightness (Cd/m2) 680 700 720 590 650 Half life (hours) >10,000 >10,000 > 10,000 > 10,000 > 10,000 Table 2 Example 6 Example 7 Example 8 Example 9 Example 10 Host material 2a · 1 2a-1 2a-1 2a-1 2a-1 Push material D-51 D-53 D-52 D-48 D-27 Drive Voltage (V) 6.0 6.0 6.0 6.0 6.0 Luminous Blue Blue Blue Blue Blue Luminous Brightness (cd/m2) 600 610 550 700 540 Half Life Lifetime (hours) > 10,000 > 10,000 > 10,000 > 10,000 > 10,000 132042. doc - 96 - 200914579 [Table 2] Table 3 Example 11 Example 12 Example 13 Example 14 Example 15 Body material 2a-1 2a-1 2a-1 2a-1 2a-1 Replacement material D-13 D-14 D-68 D-50 D-43 Drive voltage (V) 6.0 6.0 6.0 6.0 6.0 Luminous blue blue blue Color blue blue illuminance (cd/m2) 650 550 760 660 730 half life (hours) > 10,000 > 10,000 > 10,000 > 10,000 > 10,000 Table 4 Example 16 Example 17 Comparative Example 1 Comparative Example 2 Comparative Example 3 Host material 2b-9 2d-l 2a- 1 2a-1 2a-1 Dispersing material D-44 D-44 (A) (B) (c) Driving voltage (V) 6.0 6.0 6.0 6.0 6.0 Luminous color blue blue blue blue blue luminous brightness ( Cd/m2) 680 650 330 300 400 Half life (hours) 8,000 7,000 4,000 3,000 5,000 Industrial Applicability As shown in the above detailed description, the organic EL element of the aromatic amine derivative of the present invention is used at a lower level. Under the voltage, sufficient light-emitting brightness can be obtained in practical use, the luminous efficiency is high, the use is not easy to deteriorate for a long time, and the life is long. Therefore, it is used as a light source such as a flat illuminator of a flat panel television or a backlight of a display. 132042.doc -97-

Claims (1)

200914579 X. Patent application scope: It is expressed by the following general formula (I) 1. An aromatic amine derivative [Chemical Formula 1] Wherein R1 to R2 each independently represent a chlorine atom, a substituted or unsubstituted carbon group of (4), or a substituted or unsubstituted aryl group having 5 to 50 carbon atoms; R3 to R6 respectively Independently means that the substituted or unsubstituted carbon number is 丨~"the substituted or unsubstituted carbon number is 5~5〇: or the substituted or unsubstituted carbon number is 5~50 a ring group; Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl group having 5 to 5 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 5 carbon atoms, or The base represented by the above formula (A); in the formula (8), 'Ar3 and Ar4 respectively think about *t, and the substituted or unsubstituted carbon number is 5 to 50. A certain, tenth or substituted or unsubstituted carbon number of 5 to 50 divalent heterocyclic groups, R7| _ _ unsubstituted or unsubstituted carbon number 132042.doc 200914579 is a stretch of 1 to 50 Alkyl, _〇_, _s_, _s〇2, _8 say 8&9, (r R and R independently independently represent an unsubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or substituted Unsubstituted carbon number is 5~5〇 aryl)); a and b are independent of the integer of 3; & when 2 or more, multiple A〆 can be the same or different; b is 2 or more At the time, the plurals may be the same or different; R5 and R6, Arl and the other are connected to each other. R1 and R2, R1 and Ari, ... and gossip, ... and ... R5 and / or R6, Ar2 and R3 and / or ruler 4 may be bonded and or unsaturated ring respectively; and when a = b = 1, no 14 - The case of the naphthyl group, wherein R to R6 are all unsubstituted phenyl Ar and Ar2 are unsubstituted oxime, 4 phenyl or form. Ar1, 2. For example, item! The aromatic amine derivative in which Ar2 is independently a group represented by the formula (A) in the formula (1). Ar1 ^ 3 · An aromatic amine derivative as claimed, wherein Ar in the formula (1) is the same and is a group represented by the formula (A). (Claim the aromatic amine derivative of the present invention, wherein in the formula (1), the substituted or unsubstituted carbon number is from 5 to 50, which is .., .V square storm' or祌不:,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, In the formula, [132042.doc 200914579 R ~R , Ar1 and Ar2 respectively think that A is independent of the above; in the formula (), Ar and Ar4 are independently the same as above, and R7 represents -Ο-β-S 〇2_, 'SlR8R9- '-NR1()-(r8, R9 and r1. independently substituted or unsubstituted carbon number of 丨~5〇, or substituted or unsubstituted carbon number a 5 to 50 aryl)}; a and b are each independently an integer of 1; R1 and R2 may be bonded to each other to form a ring; wherein, no aromatic ring is formed; wherein, none of Ar1 and Ar2 are substituted or not Substituted oxime, 4_ benzene = I'4 extension, phenyl, naphthyl, 9,10-extension hydrazine. 6. The aromatic amine derivative of claim 1, wherein In formula (1), [where, R1 to R6 are each independently the same as above; A〆 is a group represented by the above formula (A): in the formula (A), Arj, Ar4 and R7 are each independently the same as described above; and Ar2 is independently substituted or not The substituted aryl group having 5 to 5 carbon atoms or the substituted or unsubstituted divalent heterocyclic group having 5 to 5 carbon atoms; " a is an integer of 1 to 3, and b is 2 to 3 An integer; R1 and R2 may be bonded to each other to form a ring; wherein 'except for the case of forming an aromatic ring'. 7. The aromatic amine derivative of claim 1 which is represented by the following formula (η) 132042.doc 200914579 [ 2] R11~R12 are independently the same as r1~r2; Rl3~Rl6 are independently the same as R3~V; Ar and Ar respectively represent the condensed ring group substituted or not 10~50; ^ ^ ^ carbon number is 'There is no case where Ar and Ar12 are the same; the shape "and R'2 can be linked to each other to form a ring; wherein 'there is no formation of an aromatic ring: [Chemical 3] 8. Such as - month item 7 square aromatic amine derivative , which is represented by the following general formula (in): c is not the same as above; the antimony and the knives independently indicate that the substituted or unsubstituted carbon number of the skeleton having a naphthalene residue is 1〇~5〇, B B B B B B B B B B ; Miaogongshan U 〔 衣 虱 atom, carbon number 1~4 alkyl, carbon number bC (10) ' carbon number 6 to 16 aryl; wherein, with B6, ^ B and B5, B7 and B12, B8 and B9, B9 and 132042.doc 200914579 B10, B10 disk b11's right, the group-above can be mutually fast and also ring-up, the unsaturated g ·5Γ \ , , " °, open) into unsaturated alkane The base, the carbon number is 5 atoms, the slave number is 1 to 4, the ring group of &, the aryl group having a carbon number of 6 to 16; the same case of the squad ...., the smectite and the 8 ring; R, R!2 can be: two rings; among them, the formation of benefits, the connection of objects into..., the case of making a square incense ring]. 9. Aromatic amine derivative according to claim 7: Table of the following general formula (IV) [Chemical 4] RU to Rl6 are each independently the same as above; C to C each independently represent a hydrogen atom, a carbon 5 to 6 cycloalkyl group, a carbon number of 6, an aryl group, ~C1:, a carbon number: c, c , c, c5, c, cl2, c9: cC and not full; ίσ卢·v ϋ phase-bound carbon number is == aryl; base inverse number is 5~6 ring-shaped base, carbon number is 6~ 16:: and ~ to form a ring; wherein 'there is no aromatic ring', the aromatic amine derivative of the item 7 is expressed by the following general formula (7) 132022.doc 200914579 R"~Rl6 are independently the same as above. Dl~D]4 independently represent Λ Λ, 5~6 ring 浐 & ', carbon number 1~4 alkyl, carbon D 'D3 and D4, D4盥η5 Ν 6 square base, Di and furnace, 〇 2 and D, D and 〇! 4, into the ring; and, the unsaturated ring can be connected to each other, the carbon number is 1 ～4, PI has a hydrogen atom and an aryl group independently; 4. a ring-burning group having a carbon number of 5 to 6, a carbon number of one or two and Rl2 may be linked to each other to form a ring; wherein, no aromatic ring is formed (4) More biological, its - under the "form (4) table [6] R is independently the same as above; E is independently represented by a hydrogen atom, an alkyl group having a carbon number of 1 to 4, a carbon number, a k-ring group, an aryl group having a carbon number of 6 to 16, and £1 and £6. , £3 and £4, , E, e and E4 can be interconnected to form an unsaturated ring; in addition, the 132042.doc 200914579 saturated ring can be divided into 55, delusion &> number is 5~6/ a gas atom, a carbon group having a carbon number of 1 to 4, a cycloalkyl group of carbon, an aryl group having a carbon number of 6 to 16; a non-formed aromatic ring RU and R12 may be bonded to each other to form a ring; wherein, the case]. 12. For example, the aromatic amine derivative of the formula 7 is represented by the following formula (νπ) K~R16 are each independently the same as above; f~FU independently represents a hydrogen atom, a carbon number of a ruthenium group, a ring group having a carbon number of two, and an aryl group having a number of (four), 〜6~, F> F5, FW, F, Fll, Fl2^i3, Fi, 4^ two phases are connected to form an unsaturated ring; further, the unsaturated ring can be independently carbon number, carbon number of 1~4, carbon number An aromatic group having a ring-burning group of 5 to 6 and having a number of 6 to 16; an aromatic amine derived from a mixture of the ruler 11 and the group of 4, wherein the aromatic ring is not formed by the following formula (th)] 13 · As indicated [Chemical 8] U2042.doc 200914579 The knife is independent of the above; G1~G14 eight knives independently represent hydrogen + +, stone mountain slave number is 5~6 * 妷 number is 1~4 alkyl, carbon G4, 8, carbon number is 6~16 The aryl group, G1 and G6, G3 and clothing, and the β-non-saturated ring can be divided into X 丨丨 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六 六16 aryl; Rn and R12 can be two:: ～6 of the ring-burning group, the carbon number is the case of the aromatic ring, and the phase is bonded into a ring; wherein, the unformed material amine derivative: /, 彳糸 is the following Formula (IX) 丄, Κ Κ are independently the same as above; Η independently represent a hydrogen atom, ^ m von 5~6 ring strong and h13, h, h 4 into an unsaturated ring, the unsaturated ring 132042.doc ~ 4 alkyl , carbon H1 and Η8, H4 and H9 can be linked to each other independently with hydrogenogen 200914579, carbon as i~4 alkyl, 6~16 aryl, ·45~6 cycloalkyl, carbon number R Π and R12 can choose each other. "Jes + J is connected to form a ring; 1 shape J. 〃, Τ does not form an aromatic ring] 5 • As requested by the aromatic amine derivatives, the system shows: [Chemical 10] is represented by the following general formula (X)丨~R2 are the same; R27~R26 are independently the same as R3~R0; I 〇, _S〇2-, -SiR28R29·, -NR30-(R28, the knives are independently substituted or unsubstituted carbon number is 1~ 5〇Unsubstituted carbon number is 5~5〇 aryl); 氺], RT is linked to each other into a ring; wherein, no aromatic ring is formed,]. The aromatic amine derivative of item 1, which is represented by the following formula (XI): 132042.doc 200914579 R~R32 are independently identical to ri~R2; R33~R36 are independently identical to R3~R6; R37 and R38 represent -〇-, _s-, _S〇2_, _SiR131R132_, _Nr133_ (13 13 1 t> 132 R and R each independently represent a substituted or unsubstituted aryl group having a carbon number of from 1 to 50, or a substituted or unsubstituted carbon number of 5 to 5 Å; wherein, no r37 & r38 In the same case; R 1 and R 32 may be joined to each other to form a ring; wherein, except for the case of forming an aromatic ring]. 1 7. The aromatic amine derivative of claim 1, which is represented by the following formula: [Chemical 12] R41 to R42 are independently the same as r!~r2; R43 to R46 are independently the same as r3~r6; R47 means -Ο-, -S-, _s〇2_ -SiRl41Rl42-NR143- (R4!, R, R #别Independently substituted or unsubstituted aryl group having a carbon number of U or substituted or unsubstituted aryl group having 5 to 50 carbon atoms; R41 and R42 may be bonded to each other to form a ring; wherein, soil heat is formed The case of Fang Xianghuan]. 132042.doc -10- 200914579 It is represented by the following general formula (xm). 1. 8. The aromatic amine derivative of claim 1, which means: [Chem. 13] [wherein, R51 to R52 are independently the same as Ri~R2; R~R56 are independently the same as r3~r6; R57 represents -0-(R151, R152, R is a ketone of 1 to 50, aryl); • S SO. i3 八, 犹1, 叫,·nr153_ -: independently substituted or unsubstituted carbon number substituted or unsubstituted, the amount of 5 to 50, Ar52, represents a substituted or unsubstituted group. ; a condensed ring of 10 to 5 〇 The ruler 51 and the ruler 52 can be connected to each other to form a ring; wherein, the shape]. *', the formation of an aromatic ring. 19. The aromatic amine derivative of claim i is complex representation: by the following general formula (XIV) [Chemical 14] R* \ (XIV) R« [in the formula, r61 ~r62 is independently the same as R1~R2 respectively. 132042.doc 200914579 R63~R66 are independently the same as R3~r6; Ar61 represents a condensed ring group with a substitution number of 1〇~5〇 substituted or not taken; Ar62 is The substituted or unsubstituted phenyl group and the R62 may be bonded to each other in a ring shape]. , A, without the formation of a square aroma ring 20. The aromatic 矣 _ · , ' , / , as claimed in the following formula (XV) is not [Chemical 15] Rw Ocv) [in the formula it R71 R72 Independently the same as ri~r2; R73~R76 are independently the same as R3~r6; = /〒_〇-, -S-, -S02_, -SiR171R172_, _NR"3_ (R171, R]72, R 173 gossip , γ knives 1 are independently substituted or unsubstituted alkyl groups having a carbon number of 1 to 50, or substituted or unsubstituted); substituted Ar72 71 having a carbon number of 5 to 50 is substituted or not Substituted phenyl; R and R72 may be bonded to each other to form a ring; wherein, except for.] Formation of an aromatic ring 21. The aromatic amine organism of claim 1 which is represented by the following formula (XVI): 132042 .doc -12- 200914579 [化16] Wherein R81 to R82 are independently the same as R1 to R2; R83 to R86 are each independently the same as R3 to R6; and R87 represents a substituted or unsubstituted alkyl group having a carbon number of 5, or U 22. The group -0-, -S-, -S02-, -SiR181R182_, _nr183_(r181, R182, R- are each independently substituted or unsubstituted carbon number, or substituted or unsubstituted a substituted aryl group having a carbon number of 5 to 50; Ar 82 represents a substituted or unsubstituted aryl group having a carbon number of 5 to 5 Å, or a substituted or unsubstituted carbon number of 5 to 5 Å. a divalent heterocyclic group; the soil a is an integer of 1 to 3, and b is an integer of 2 to 3; and R71 and R72 may be bonded to each other to form a ring without forming an aromatic ring; It is an aromatic amine derivative of the following formula (XVII), which is referred to as Item 1, and represents: [Chem. 17] R 1 to R 92 are independently the same as ri~r2; R93 to R96 are independently the same as R3 to R6; 132042.doc • 13- 200914579 R97 indicates that the substituted or unsubstituted carbon number is 丨~“alkylene, Or 〇_, -S-, -S02-, -SiR191R192-, r192, π 1 9 3 independently as a substituted or unsubstituted alkyl group having a carbon number of 5, or substituted or not The substituted aryl group having a carbon number of 5 to 5 Å); X each independently represents a single bond, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, and a carbon number of 6 An aryl group of ~16; wherein, χ4χ2, β and χ3, f and γ, χ, χ6, χ6Μχ7, 乂7 and 乂8 of f. 彳, 'and the above may be linked to each other to form an unsaturated ring, and the unsaturated The ring may independently have a single bond, a hydrogen atom, a carbon number of 4, a cycloalkyl group having a carbon number of 5 to 6, and an aryl group having a carbon number of 6 to 16; Ar 92 represents a substituted or unsubstituted group. a divalent heterocyclic group having a carbon number of 5 to 5 Å, a substituted or unsubstituted carbon number of 5 to 5 Å; a being an integer of 1 to 3, and b is an integer of 1 to 3; ]R and R" can be linked to each other Into the ring; wherein, there is no formation of an aromatic ring 〇 23. ^ to the item i of the aromatic amine derivative, which is represented by the following formula π species) - [Chem. 18] R 1 to R 102 are independently the same as Ri to R 2; R! 〇 3 to R 丨 ° 6 are independently the same as r3 to r6; [wherein, 132042.doc -14- 200914579 R107 and R1G8 respectively represent substituted 1 π夕妯r Λ七土一°, the carbon number of the work is replaced by the extension of the 50, or · 〇 _, _ υ〇 2 ·, training - NR193- (R191, R192, RH3 points -, the carbon number is 50 calcined base, or hydrazine substituted 5~5. aryl); Lai Weifeng carbon number is X11~X18 and X21~X28 respectively molybdenum A 士β independently represents a single bond, a hydrogen atom, a carbon number of 1~4 The alkyl group has a carbon number of <; an alkyl group having a number of 5 to 6 and an aryl group having a carbon number of 6 to 16; wherein, X" and Xl2, X12 and X13, X" and ΧΜ, χ^χ16 Χ,6#Χ,7'Χ,7^Χ,8'χ2^Χ^Χ^χ^χ23:χ2; X25 and X26, X26 and Χ27, χ27盥”, /, any one or more of the groups are connected to each other Unsaturated ring; further, the ^4 ^ ° Hai unsaturated core can independently have a single bond, a hydrogen atom, an alkane having a carbon number of 1 to 4, and a cycloalkyl group having an inverse number of 5 to 6 An aryl group having a carbon number of 6 to 16; 'a is 1 to 3 The number b is an integer from 1 to 3; R01 and rW2 can be connected to each other. #援+, 埂, °°%, wherein no aromatic ring is formed.] 24. If the item 7 is The aromatic amine derivative according to any one of 23, wherein in the above formula (II) to (XVIII), r13 to ri6, r23 to r26, R33 to R36, and R43 R46. 53 "R, R to R, R63 R66, R73 to R76, R to R86, r93 to r96, r, °3 to r, and 6 are unsubstituted phenyl groups. A. The aromatic amine derivative of claim 1, which is a doping material for an organic electroluminescence device. 26. An organic electroluminescent device that has an organic thin film layer comprising a layer or a plurality of layers including a light-emitting layer between J and an anode, and a layer of I32042.doc •15·200914579 containing the organic film At least the creature of the layer. In the aromatic amine derivative of claim 1, the above-mentioned light-emitting layer contains 2 7. The organic electroluminescent device of the item 26 is an aromatic amine derivative. 28. The organic electroluminescent excitation element of claim 17, wherein the luminescent layer comprises the above-mentioned sulphur amine derivative, and the sulphate-A compound and a compound having a structure represented by the fluorene-center skeleton formula (2a): , a [Chem. 19] a group derived from an aromatic ring of 6 to 20, and the substituted 111 of r111~r are each independently an aryl group selected from a hydrogen atom, a substituted or unsubstituted carbon number of 6 to 5 Å, a substituted or unsubstituted heteroaryl group having 4 to 5 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number of 3 to 50 The alkyl group, the substituted or unsubstituted carbon number is an alkoxy group of 丨~5〇, a substituted or unsubstituted aralkyl group (the carbon number of the aryl moiety is 6 to 50, and the carbon of the alkyl moiety) a substituted or unsubstituted stone having an inverse number of 5 to 50, a substituted or unsubstituted arylthio group having a carbon number of from 50 to 50, substituted or unsubstituted Alkoxycarbonyl (the number of charcoal in the alkyl moiety is 1 to 50), substituted or unsubstituted sulphuric acid, sulphur, dentate, cyano, nitro and thiol groups . 132042.doc -16 - 200914579 29. 30. The organic t-excitation element of claim 28, wherein in the above formula (2a), 'Ar11 and Ar.12 are different. The organic electroluminescent device of claim 26, wherein the luminescent layer contains the aromatic amine derivative and a compound having a structure represented by the following formula (2b) including a fluorene center skeleton: [Chem. 20] m (wherein, Ar13 and Ar14 are each independently a substituted or unsubstituted aryl group having a carbon number of 6 50, and L and L2 are each independently selected from a substituted or unsubstituted phenyl group, substituted or not Substituted naphthyl (y-form), substituted or unsubstituted exo group, and substituted or unsubstituted dibenzoxanthene dibenz〇sil〇lylene Base, mA〇~2 31. Integer, η is an integer from 1 to 4, 8 is an integer from 〇 to 2, an integer from ^〇 to 4, and L or Ar is bonded to any of 丨~5 In position, L2 or the key is placed at any position of 6 to 10 of the )). The organic electroluminescent device according to claim 26, wherein the luminescent layer contains the above aromatic amine derivative and a compound having a structure represented by the following formula (2c) containing a triphenylamine skeleton: [Chem. 21] 132042.doc -17- 200914579 f The group in the base of the box, R19 to R21 respectively represent a hydrogen atom or a substituent. Η蜀32. The organic galvanic material of claim 26, wherein the above-mentioned hair layer contains ^m. ^ / , and has a compound represented by the following formula (2d) : < [Chem. 22] V (2φ I At Α<» _ Al" Ar independently represents an aryl group having a carbon number of 6 to 50, and & represents a derivative derived from an aromatic ring or a heteroaromatic ring. Price group] 33 - a solution containing an organic electroluminescent material, which contains an organic electroluminescent material such as a request for an aromatic amine I, and a solvent as an organic electroluminescent material. a solution of an excitation light material, wherein the organic electroluminescent material comprises a material and a dopant material, and the dopant material is an aromatic amine derivative of claim 1, wherein the host material is selected from the group consisting of (d) the compound represented, the compound of the formula (2b) of claim 2, the compound of the formula (2C) as claimed in claim 31, and the formula (iv) of claim 32. At least one of the compounds listed. 132042.doc •18· 200914579 VII. FIG designated representative of: (a) :( no case designated representative graph) (ii) of the present symbol elements representative diagram of a brief description: eight, when the case if the formula, please disclosed invention features most indicative of the formula: 132042.doc